My life completely changed this year.
At the beginning of the year, Write of Passage was a middling lifestyle business. I’d planned to keep the team small and run two cohorts per year. Some conversations in the spring changed my thinking. I stopped Hugging the X-Axis and went all in on the company. I hired a talented executive team, built a production studio in Austin, and grew the team from four full-timers at the beginning of the year to 22 at the end.
Growing the company so quickly has been exciting and stressful. I’ve experienced elation and defeat within moments of each other. Most of the time, I’ve enjoyed it. I’m proud of our vision, our culture, and our product. Never in my life have I experienced such tight alignment between my values, my work, and my interests. Leading this company is absolutely intoxicating.
At times, it’s been tormenting. My focus has taken a hit in particular. All the things coming my way has my attention scattered like a sidewalk pigeon. Creatively, I’ve suffered. My writing has taken the biggest hit. Focusing so much on the company has also distanced me from friends and family as a result.
One surprise is how much business comes down to people. Turns out, there’s less alpha than expected in “being good at business” and more alpha than expected in understanding human behavior.
I’ve had to confront my shortcomings as a leader (and a person). An aversion to conflict is one. In the past, I’ve retreated into silence instead of saying what I think. Like the time my friend Sam pantsed me on the basketball court in 3rd grade and I didn’t call him out for it. These conflicts have actual consequences now though. Bad things happen if I don’t confront the tension. What looks like compassion in the short term can lead to destruction in the long term.
This Annual Review is about the lessons I’ve learned running Write of Passage this year. It’s about my successes and my failures, my joys and my struggles, my dreams and my regrets. I’ve structured it in multiple sections. I’ll begin by reflecting on the goals I set at the beginning of the year. Then I’ll set new goals for 2023. At the end, I’ll share the best lessons I learned this year too.
Reflecting on 2022 Goals
100,000 Email Subscribers + Sustain Writing Momentum
Ugh. I botched things here. My email list only grew by 15,000 people, I tweeted less than at any point in the last seven years, and only published one long-form essay during the second half of the year.
Prioritizing the business was largely to blame. Growing the team and solidifying our ways of working required a bunch of focus. Much of my deep work time went to recruiting, company structure, internal meetings, and memos like our company vision. Tactically, I don’t do a good job of staying off Slack, email, and iMessage while writing. All the inbound was crippling. I was too often “Distracted David.”
I also didn’t manage my schedule as effectively as I had in the past. For the entirety of my career, I’d written for 90 minutes every day. I lost the habit this year. Even when I found the time to write, I was much less focused. My fulfillment and the revenue growth of Write of Passage suffered as a result (oh, the irony of not being able to write because you’re teaching people how to write シ).
Many of my creative blocks were emotional. At times, I was so stressed out about what was happening inside the company that I lacked the headspace to focus on writing. My emotions were too turbulent, almost purposefully so, which I regret. Coming into the year, I believed that effective leadership came from matching the emotional swings of people on my team. When people were anxious, I got anxious. When people were riled up, I got riled up. I thought this was a good thing.
And boy, was I wrong. The truth is exactly the opposite. Effective leadership is about staying calm when things are haywire. It’s the business equivalent of Napoleon’s definition of a military genius: “The man who can do the average thing when everyone else around him is losing his mind.”
Part of being calmer is having faith that things will be okay. It’s like airplane turbulence. The first few times, you freak out. Then you realize it’s par for the course (and subsequently laugh at all the people who are freaking out next to you).
To meet my commitments, I felt an increasing need to justify everything on my schedule. Instead of writing what I wanted to write about, I started writing about what I should write about. This stifled me. The problem is that the most personally impactful essays are the byproduct of an intellectual breakthrough. You can’t rationalize your way to one.
To be maximally creative, you have to invite the muses into your heart, and trying to justify all your intellectual intuitions is the surest way to turn them away. It’s no coincidence that the venn-diagram between mystics and intellectual pioneers has so much overlap. David Bowie literally believed he was an alien; Einstein was obsessed with an occult researcher named Helena Blavatsky; Nikola Tesla claimed he received ideas out of conversations with radios; John Rockefeller believed he was doing God’s work by making oil; Schrodinger discovered his famous equation during a camping trip, where he traversed deep into the woods alone, put pearls in his ears to block out sound, and discovered the equation that forever changed quantum mechanics; Paul Dirac said his eponymous equation came to him out of a fire, where the flames spoke to him and showed him the equation (these examples are from this excellent essay).
All these innovators met their muse.
From a writing perspective, this year wasn’t a complete failure though. I’m exceptionally proud of the Ultimate Guide to Writing. I clearly articulated my feelings about Austin in this essay (and offended a lot of people in the process). Shorter articles like 28 Pieces of Life Advice and my conveyor belt theory of education also crystalized ideas that’d been brewing in my head for a long time.
Such an unproductive writing year can’t happen again though. Writing in public is some of the most fulfilling work I do. As of now, it’s also the main growth channel for Write of Passage. I’m planning to make some serious changes for next year.
Hire an Executive Team for Write of Passage
When I started the year, nearly everything in my business was linked with Tiago Forte. We shared a team for three years. The partnership was a creative solution to the cyclicality of online course businesses. Both of us only ran a few cohorts per year. We only needed staff when we were actually running a cohort. The rest of the year, we wanted to be left alone to write and grow our audiences. Knowing that quality people would only work for us if we offered them full-time work, our employees oscillated between our courses. Disbanding our partnership at the beginning of 2022 was tactically and emotionally arduous.
The operational tasks were particularly challenging. When you run a business, there’s so much you have to think about besides the actual work of delivering your product — taxes, payroll, legal, corporate structure, retreat planning, reimbursements, ways of working, software tooling, and more. Finding help was my priority for the first half of 2022.
We hired an executive search team to find us a VP of Operations. On the advice of Andrew Wilkinson, I insisted on somebody who’d done the job before. In this case, they needed to have grown an online education company to eight figures in annual revenue as their head of operations. We must have interviewed eighty candidates in what felt like a total odyssey. Five months after starting the search, we hired Chris Monk. Today, he is the backbone of Write of Passage. Hiring him was one of my biggest wins of the year, and I sleep deeper at night with him onboard.
The second half of the year was devoted to hiring a VP of Marketing. This hiring process was much more difficult. Marketing hires are nebulous and the work is tough to quantify, which makes it hard to gauge competence. For months, we had no momentum. Sharing the job description felt like putting bait into a pond without fish. Then Erin Acheson magically showed up. We felt the spark immediately, built a relationship with her quickly, flew her down to Austin for a series of in-person conversations, drove her a little insane with all our questions, and signed the dotted line the day after. She still ribs me for the pandamonium of it all, but hey, I’m protective over the culture. Sorry not sorry!
So far, here’s what I like about the way our executive team operates: We’re jovial, but unafraid to call each other out for being wrong. We’re aligned enough to march in the same direction, but distinct enough to embrace the productive tension that leads to effective decision-making. Our debates are intense, but respectful. We’re still maturing though. Philosophically, we’re still learning when to speed up and when to be patient; when to be stern and when to be compassionate; how to scale the company in a Write of Passage-y fashion.
Study the Bible
This didn’t happen. I got bored of my Bible study. Though I liked how much it was focused on the text, the conversations didn’t keep me engaged. I also only met with my Rabbi once during the second half of the year.
Next year, I’d like to resume these studies with a deeper focus on the primary texts. To study Judaism, I’ll set a game plan with my Rabbi at the start of the year. To study Christianity, I’ll organize my own reading group with local pastors, scholars, and seekers instead of attending the same Bible study.
Personal Goals for 2023
Creating an Emotional Experience for Readers
The inspiration came from a yet-to-be-released How I Write interview with Riva Tez. She writes as well as anybody I follow online. Her words hit me at a sensory level, as well as an intellectual one because of the way she uses such vivid language and metaphors. Some of her most profound paragraphs even break down when you analyze them logically.
Take a sentence like: “The American Dream has been replaced by mass-packaged mediocrity porn, encouraging us to revel like happy pigs in our own meekness.”
The whimsical SAT words that we’re taught to associate with impressive writing are nowhere to be found here. The words are easy to understand on their own, but collectively, she’s sown them into a vivid tapestry tattoos a lasting image in the reader’s mind. Such lively writing is more likely to stick because the salience of memory is tied more to emotion than truth.
Morgan Housel said this line to me, and I can’t stop thinking about it.
I want my personal writing to transcend clarity and logic in order to bypass my reader’s intellectual core and resonate at a deeper and more visceral level. Poets do this. Novelists do this. Some obscure Internet writers do it too.1 But in the non-fiction / techy / business / self-helpy sphere where I devote most of my attention, this sensorial writing is almost nowhere to be found.
How am I going to acquire this skill?
I will read the writers I admire and break down what they do well (David Foster Wallace, and Gregory David Roberts spring to mind). How do they shape their sentences? What words do they choose? When do they prioritize clarity, and when do they turn to metaphor?
Whenever possible, I’ll quantify their approach and trust that it will rub off on me through a process of osmosis. I’ll adopt an intuitive posture once it’s time to write again — because peak creativity comes from an intuitive place, not an analytical one.
Redesign my Personal Website
My website should be the ultimate embodiment of what we teach at Write of Passage. It should be the digital expression of who I am and what I stand for. It should be unmistakably mine in a way that enhances the ideas instead of taking away from them. My current website falls short of these standards. I want my site to feel like my living room, where style and substance enhance each other (all the way down to how footnotes are displayed and the email capture forms are designed).
I’m tired of minimalism. I don’t want to chase it, even if it comes at the expense of wide-scale reach, which strips the soul out of design in the name of virality and search-engine optimization.
I want my site to feel like a smorgasbord between the SMEG + Dolce & Gabbana collaboration for kitchen appliances, Art Deco statues, the color palette of Italian futurism, the joyous (but classical) aesthetics of Disneyland, late-stage impressionism, Thomas Cole’s dreamy and Eden-esque landscapes, Celtic calligraphy, a cozy study with mahogany wood, Gaudí sketches, Madeon visuals, the Trinity University Library in Dublin, and French interior design.
Improving My Taste
Good taste becomes a differentiator at the highest levels of success, but I know so few people who strive to improve their taste. Though reasonable minds can disagree on what quality looks like, hierarchies of value absolutely exist, and you’d be a fool to think otherwise. This becomes obvious once you start creating things.
I’d like to improve my taste for people so I can better identify people who should work at Write of Passage. One of my favorite interview questions has become: “How do you cultivate your taste?” If the person I’m talking to is serious about their craft, they’ll light up and give an inspired answer.
Here are some of the best hiring heuristics I discovered this year:
- Good people speak in specifics: They can simultaneously look at the big picture and put their boots to the ground. When they zoom into the work, they’ll mention details you never even thought to consider. Beware of charismatic people who only speak in lofty abstractions.
- Exceptional people are magical: They continually surprise you. You chuckle when you see their work because they deliver things you would’ve never thought to ask for.
- Do real-work tasks: Standard hiring processes over-index on the candidate’s ability to interview well. Real-work tasks are the best way to filter out people who speak well, but don’t do good work. Use timed tasks whenever possible so you can see what people can accomplish in a set amount of time.
I’ve spent the better part of a decade honing my taste for what quality Internet writing looks like too. All those miles of scrolling Twitter came up clutch this year when I discovered The Cultural Tutor and brought him on as our Writer-in-Residence at Write of Passage.
He’d only been writing for six weeks when we first met. He’d just published a Twitter thread to announce the launch of a new subscription email newsletter. Given his trajectory, I thought it was a terrible idea because the majority of what he’d publish would hide behind a paywall, which would slow his audience growth. Little did I realize that he was the archetype of a starving artist. In our first interaction, he was broke and living with his parents. To earn a little cash, he’d recently worked at McDonalds during the day and the overnight shift at his alma mater, where he’d read and write through fluorescent-lit nights. 15 minutes into my first conversation with him, I offered him an annual wage so he could focus full-time on writing. Eight months after publishing his first tweet, he has more than 1 million followers and runs one of the fastest growing Twitter accounts in the world.
I’d also like to develop my creative taste. Jerry Seinfeld nailed it when he called “taste” and “discernment” the twin skills of a quality artist. He says: “It’s one thing to create. [You also] have to choose. ‘What are we going to do? What are we not going to do?’ This is a gigantic aspect of artistic survival.”
Here’s are some of the ways I actively improve my taste:
- I write in public.
- I write every day.
- I choose what to read based on what’s well-written as well as what’s informative. I deconstruct what I like and emulate my favorite writers.2
- I travel to cities where the locals have excelled in some domain, and try to understand why it’s a nexus for innovation. Culture may be subjective and hard to quantify, but sustained outsized success in a given domain certainly isn’t random. I try to write about cities whenever I visit them (such as Austin, Montreal, and Detroit).
- I do everything I can to surround myself with high performers. No matter what they excel at, they almost all carry themselves in the same way, and I want to soak up everything there is to learn by sucking from the straw of wisdom. And hopefully, I can return the favor too.
- “Your taste for design lags far behind your ambition” was one of the more difficult pieces of advice I received this year. It hurt because it’s true. The crazy thing is I’m much better than I used to be. I take a Lindy approach to cultivating my taste in aesthetics. I ignore almost everything modern and study the classics instead. I even have a Twitter list devoted to classic art that I browse almost every day. I spend an unreasonable amount of time in art museums and watching art history documentaries.3 The interior designer I work with in Austin has also elevated my sense of taste.
This is why I’ve spent so much time studying Shantaram.
Shock of the New is my all-time favorite.
Over a long time horizon, “cultivating good taste” is a good one-liner for my career. This applies to taste in people, products, businesses, writing, speaking, storytelling, design. Everything. Refining my nose for quality is a daily discipline for me.
Go to the Source
If I’m going to run a remote company, I’d better take advantage of it by traveling. Western Europe’s been calling my name. I think it’s because Americans have an under-developed sense of beauty. No American city comes close to giving you the kind of reverberant awe I felt during my recent trip to Paris. Harriet Beecher Stowe came to the same conclusion when she visited Paris in 1854. Reflecting on her birthplace, she wrote, “With all New England’s earnestness and practical efficiency, there is a long withering of the soul’s more ethereal part—a crushing out of the beautiful—which is horrible.”
Paris’ imperial grandeur is magnificent. The locals know it. Tourists know it too, which is why it’s the most visited city in the world.
Though the French are borderline snobby about their culture, they didn’t always respect it. In the 16th and 17th centuries, they envied the Italians who had finer paintings and higher quality marble. Seeing all the Italian art was the most surprising part of visiting the Louvre. The museum holds the world’s largest collection of da Vinci paintings. The senate palace is a literal copy of the Pitti Palace in Florence.
Whenever things I admire cluster in a geographic location, I always try to visit. “Go to the source” is some of the best learning advice I know. Just as it helps to read the books that inspired your favorite authors, it’s worth visiting the geographical origins of your favorite art movements.
In 2022, before Paris, I also visited the West of Ireland, where my favorite poet John O’Donahue once lived. In 2023, I plan to visit Florence to learn about the linkages between French and Italian art.
While I’m there, I’d also like to tour the Brunello Cucinelli headquarters in Solomeo and meet some of the higher-ups there. I haven’t found a company that better balances the desire to do excellent work with an appreciation for beauty and the desire to honor the human spirit. They don’t just make fine cashmere. They work with the kind of dignity I’d like to emulate.
Our human spirit comes alive when we’re surrounded by care. If you’re making something for a number on a spreadsheet, you’ll focus only on utility. But if you care about the person you’re making something for, you’ll transcend what can rationally be justified and make something to uplift their spirit.
A lack of man-made beauty is the hardest part about living in Austin for me. I love the people, but my artistic spirit feels dead here. The crude built environment is what you get in a Godless world of hyper-individualism and short time horizons.
I love books, but there’s so much they can’t express. When a friend visited Florence earlier this year, she said: “You can read about power all you want, but you can’t appreciate it until you visit the marble-filled, Michelangelo-decorated tombs of the Medici family. The grand statues and towering ceilings will make you feel the weight of your own insignificance.”
Moments like that are why I’d like to visit.
Company Goals for 2023
Flagship: Our Program for Adults
Coming into the year, just about everything about our Flagship product was stuck in my co-founder Will Mannon’s head. This was unsustainable, both for him and the company. We joke that the product felt like it was hanging from a string. If that string had been cut, it would’ve all fallen to the ground.
In the spring, we hired Dan Sleeman as our Director of Flagship. He spent the year operationalizing the product. He also built the infrastructure to track student writing and ensure that every piece of student writing receives feedback from our team.
We also defined our core commitments:
- Publish Quality Ideas: Mediocre writing won’t get you anywhere in the GPT age. We help you write things only you could’ve written. The better your writing, the better the opportunities that’ll come your way too.
- Find Your People: You’ll meet your closest friends by taking Write of Passage and sharing ideas in public.
- 2x Your Potential: We help students double their income, double their creativity, and find work that’s twice as meaningful.
The core commitments have made shaping our Flagship product much easier. It was the first time we were explicit about what we stand for. Before our commitments, we’d freak out whenever somebody asked for a refund. We’d re-evaluate the product, our sales strategy, and sometimes our worth as human beings. Now, we’re calmer about refund requests. Since most of the people who ask for refunds have buyer’s remorse or bought the wrong product, we’re much more comfortable saying “this product isn’t for you” and giving them their money back. But when we fail to deliver on our core commitments, we take it very seriously.
For 2023, we have two main goals: 1,000 full-paying students + second paid product to help people improve their writing and grow their audience between cohorts.
With each successive cohort, I’d also like the student experience to depend on me less.
We’ve also started working on an “Outplacement” program to match students with jobs. We tested it with Jim O’Shaughnessy. He funded 15 full-ride scholarships for Write of Passage. In return, we sent him people who’d be good candidates for writing internships at O’Shaughnessy Ventures. Jim wrote: “I am not exaggerating when I say I was BLOWN AWAY by the talented people he sent our way.” He planned to hire two students. But he was so impressed that he hired three.
Our outplacement program is turning into a full-on revenue stream. Think of it like the “career services” center at a university. We’re now working with three more companies to help them find public and internal-facing writers. By March, we’ll have somebody running the program full-time. If you’d like our help finding writers, send me an email or a DM on Twitter.
Liftoff: Our Program for High Schoolers
Liftoff started slowly. My audience wasn’t as receptive to it as we expected and having only sixteen students join the beta program was a punch in the gut. We still want to help high schoolers write online but need a new way to attract them.
The most ambitious kids still apply to college. It’s the way of the world, and we’re going to use it to our advantage. With an estimated 80% of colleges that won’t require SAT or ACT scores for 2023 applicants, college essays are becoming more important. We are well positioned to help students write theirs. Students will find us through paid college essay workshops. Our goal is to make them so productive and enjoyable that our participants will itch to join the full Liftoff program and write with us consistently.
For the year, we want 2,000 paid students to join a workshop or a cohort. We want 80% of them to submit their college essays with something they wrote in Liftoff.
We’d also like to have 200 students in our Liftoff cohort by the end of the year.
Peter Thiel’s famous interview question is: “What important truth do very few people agree with you on?”
Our answer is that in the age of the Internet, big classes are better than smaller ones. Education products can now improve as they grow. For starters, my experience is basically the same regardless of how many students have tuned in. The more students we have, the more we can invest in production. A cohort with thousands of students makes it easier to meet people on your intellectual wavelength, which is why we eventually want to have thousands of students in our Liftoff program.4 At that scale, we can hire a team to provide 24/7 editing support. Students will be able to submit their essay before going to sleep and get it edited by the time they’re awake.
Ambitious high schoolers are seriously underestimated. They’re capable, but lack support. Their teachers underestimate them, their parents don’t know what to do with them, and their friends don’t share their passions. At school, they’re taught that individualism is a bad thing. They’re told to follow the syllabus instead of their innate curiosities. We want to encourage the opposite. One high schooler I spoke with (who’s an exceptional writer) hasn’t told anybody about her blog except for her best friend because she doesn’t want to be made fun of. There are tens of thousands of students like her. For them, Liftoff will be an oasis.
We’re working up to 100 students at once. Once we reach that milestone, we plan to increase the cap by 25 people each time. We won’t increase the cap unless we’re happy with the quality of our students, the way they interact, and the culture of the cohort.
Build an Independent Media Company
Until now, we’ve had a single-minded focus on product. Nearly every new hire we made helped us run our courses better. Growing the student body was mostly an afterthought. The focus paid off. Four years after starting Write of Passage, we’ve finally developed a sturdy system for building and improving our courses. There’s a bunch of work to be done, but the (very) basic foundation is in place.
We’ve cracked something with education. We teach in ways the establishment system won’t and cannot do.
We currently teach ~600 students per year. We’d eventually like to teach 10,000. In order to do that, we need to increase our reach.
Having a direct relationship with students is the first step. We don’t want to rely on the mainstream media for reach. They’re too invested in the status quo. The reporting is lazier now than it used to be (which is why I dropped out of the journalism track in college). We’re also going to route around the school system instead of working through it. Getting swept up in the cobwebs of the education establishment will slow us down and stop us from innovating until, eventually, we’re swimming in glue. The core ingredients are a company email list with hundreds of thousands of engaged subscribers, an armada of successful alums, a top-notch curriculum, essays that outline our approach, a podcast to attract high-level writers, and videos that show what it feels like to be a Write of Passage student.
It’s not enough to have good ideas about fixing education. We need people to actually take our courses.
The current education system is sorely broken. Kids hate school, the textbook industry is a sham, grade inflation is rampant, standardized test scores are falling, and end of semester surveys at many universities are used for budgeting purposes instead of improving the student experience. Doing more of what we’re already doing won’t solve much. For-profit education is the best way to fix the system.
The system is constrained by its own paltry economics. Talented people want to make money. If education companies can’t pay meaty wages, top talent will defect to industries that can (like law, tech, consulting, or private equity). Finding profitable business models for education is the first step to sustainably attract top talent.
If we’re profitable, we can also ensure that everybody who needs to be in our programs can join — no matter where they come from or how much money they have.
To make the changes we need to make, we need to focus on marketing and production:
Building a great product isn’t enough to change the education system. We have to become great marketers too.
Steve Jobs comes to mind. It’s easy to think iPods, iPhones, or the computer you’re reading this on were inevitable in retrospect. But they only exist because of Jobs’ vision. When he started in Silicon Valley, computer geeks didn’t understand why people would want ready-made computers. They liked the industrial aesthetic too. Jobs saw things differently. He wanted computers to be elegant and beautiful. To realize his vision, he had to warm ordinary people up to the idea of personal computing. Every week, he hosted a three-hour meeting with his marketing and creative team. He personally approved each commercial print ad and billboard. Though the specifics of his approach aren’t my style, the spirit of it definitely is. Apple spent 100 times more than every other company combined advertising their music player. I don’t remember Zune ads and I don’t remember Walkman ads, but I sure as hell remember the dancing silhouettes in the iPod ads. Apple has done more to make technology cool than any other company.
I see parallels between the early days of computing and the education industry today. Like early computers, the idea of school needs a rebrand. The way schools advertise themselves is as stale as their teaching. Just as Jobs pioneered the idea that computers could be beautiful and powerful, we can pioneer the idea that education can be fun and effective.
By the end of the year, we want to have 50,000 new email subscribers (and a 50% open rate) on a Flagship email list, and 20,000 subscribers on the Liftoff one. Marketing is also responsible for getting 1,000 students into our Flagship course and 2,000 students into a Liftoff program.
A savvy production team is a force multiplier for our marketing and product efforts.
Much of marketing is downstream of production. Like a space mission, production has required a bunch of work before launch. We spent six months this year building a full-on production studio in Austin, Texas. The gear is top-notch and the set is a teacher’s dream. Aesthetically, it’s a hyper-maximalist ode to beauty and creative excellence. Nothing so far has pumped me up more than a guest who described the studio as a “religious experience.”
We’re producing videos from the studio too. To date, we’ve struggled to communicate the energy with text on a website. Students repeatedly say they didn’t understand the Write of Passage magic until the first live session. Video is a more effective way to outline the experience, which is why we’re spinning up a production team.
Our production team will help with the product too. At the end of the day, we don’t compete with other schools. We compete with Netflix, YouTube, TikTok, and video games. If we’re going to win the attention battle against them, we have to make it fun to learn writing. We want our courses to be delicious and nutritious. Think back to your favorite teachers. In addition to being subject-matter experts, they were funny and captivating storytellers (Richard Feynman is a prime example).
I dream of changing the learning experience like Walt Disney changed amusement parks. Before Disneyland, amusement park employees coldly referred to their visitors as “marks.” Walt rejected the conventional wisdom. To create a warmer and more hospitable environment, he insisted on calling them “guests.” Instead of hiring industry experts, he brought in people from his movie studio. Imagining the park, he said: “Disneyland will be something of a fair, an exhibition, a playground, a community center, a museum of living facts, and a showplace of beauty and magic.”
Why can’t Write of Passage be the same?
How I Write Podcast
In the spirit of a Steve Jobs presentation, there’s “one more thing.” As part of the independent media company initiative, I’m launching a podcast called How I Write. Think of it like How I Built This, but for writing. Writers always do a podcast tour when they release a book, but never talk about their process for writing it. They only talk about the content of the book. In addition to interviewing my favorite published authors, I’ll interview online writers who embody the Write of Passage ethos.
The plan is to record most interviews in person. I’ll only record remotely if I really can’t be in the same physical location as my guest. In-person interviews inspire friendlier feelings of camaraderie and open up the potential for video. In advance of our launch, we’ve hired a full-time podcast producer and an insanely talented video editor to produce clips for the show.
Key goal: 30 episodes + 500,000 downloads by year’s end.
Solidify the Company Culture
Culture is the least tangible part of building a company, but arguably the most important. Watching the company 5x in size in one year has me paranoid about losing our gusto. I’m an absolute hawk about it. New employees can’t join without an
interrogation interview from me. I’d faster blow up the company than lose our intensity and surrender to the creep of corporate mediocrity.
If you’re going to work with us, you have to be all in. You have to think deeply, work swiftly, care personally, have a flaming heart, and hold yourself to exceptionally high standards. Most people won’t like working here, but if somebody’s a fit, the outcomes have been supercalifragilisticexpialidocious.
Something is always off-kilter when you run a company. Conflict and confrontation are everyday occurrences. Somebody’s always agitated. Somebody’s always going through a hard time. If you demand total order and calmness, you won’t get anything done. Most people get angsty when something is wrong. Great CEOs don’t get distraught. They lean into the barrage of problems in their purview. Learning to navigate conflict and make hard decisions fast is the price of entry for running a successful company.
Unfortunately, a few of our hires haven’t worked out. Through trial-and-error, we’ve learned that people who thrive at Write of Passage relish an ever-present waterfall of information. They’re voracious readers who write well and enjoy doing so. Since we move at Internet speed and operate transparently, it’s a hard place to work for people who are easily overwhelmed by a lot of information.
When we saw the benefits of direct feedback, we embraced Radical Candor — the combination of caring personally and challenging directly — as one of our Ways of Working. Radical Candor isn’t some bumper sticker idea. In fact, as we’ve learned the hard way, it’s a jarring transition for people who’ve spent their work lives in a Dilbert comic. They’re not used to giving and receiving direct feedback, and they’re definitely not used to speaking so honestly with their managers or the CEO.
Radical Candor isn’t just about criticism. It’s also about praising others (which is often more effective). The best feedback is specific. If it’s critical, it should come with a concrete suggestion for how to improve.
Radical Candor takes time to understand. When people hear Radical Candor, they default to worrying about “Obnoxious Aggression.” They think of the military sergeant who withholds praise and scolds their lieutenant for making an honest mistake.
Most tech and education companies suffer more from “Ruinous Empathy” though. They run from difficult conversations, for fear of hurting another person’s feelings. Anger pents up inside. Frustrations go uncommunicated. Nobody says what needs to be said. Even the praise feels hollow and sometimes, vaguely condescending too. Like the well-meaning parent who refuses to discipline their kids in the name of love, they do what’s easy in the short-term but destructive in the long-term. The result is a political culture filled with third-rail topics, where people talk behind each other’s back and get unexpectedly fired without any feedback in advance. Thanks, but no thanks.
There were multiple times this year when a message was poorly received on Slack. Text is a lossy medium. Messages will be interpreted in the harshest possible way, especially before you’ve gotten to know the other person. The recipient can’t see the smirk that comes with the snark. Videos and voice memos can help. So does picking up the phone and calling somebody like it’s 1983 or something. I even hopped on an airplane to have a few conversations because they required the delicacy of a high-resolution, in-person conversation.
To combat these challenges, I encourage everybody to be earnest and exceptionally kind in text communication (even if it’s a little over the top) until they have a strong relationship with the person they’re writing to.
For difficult conversations, the best mantra I learned this year is: “High care, high empathy, low emotion.”
- High care: Difficult conversations go better when you genuinely care about the other person. People can feel when you’re really listening or when you’re treating them like a pawn.
- High empathy: This is about looking at the whole person in front of you. People don’t just work for Write of Passage. They have families, friends, dreams, pains, and challenges outside of work.
- Low emotion: This is the toughest one for me. All of my hardest conversations have an emotional undertone. People come to me when they’re angry, anxious, nervous, insecure, and frustrated. As a leader, I need to stay calm so I can soberly confront the situation.5
Barack Obama once said that when you’re president, only the hardest questions land on your desk. It’ll only climb the ranks if others can’t answer it, and by the time a problem makes it to him, all the proposed solutions are bad. The same is true for a company (though the problems are much more benign).
I aspire to be the combo of Spock and Mother Teresa. Most managers get it backwards. When somebody isn’t performing, they’re like Mother Teresa and refuse to provide direct feedback. Then, one day, when they let go of the person, they become as cold, distant, and half-human as Spock. Do the opposite. When somebody isn’t performing, be like Spock. Speak truthfully. Tell the other person what’s not working. Paint an objective picture for what success looks like. If it still doesn’t work out and you have to let them go, be like Mother Teresa. Lead with compassion, support their transition, and earnestly offer to help them find their next job.
Or, as one friend said after a few beers: Don’t blow smoke up people’s ass while they’re working for you, only to kick them out the door later.
Radical Candor flows more naturally once these habits are in place. A piece of positive or negative feedback is shared in almost every meeting I have. I’ve found it much easier to trust people who proactively critique themselves and earnestly define how they’re going to improve. “Everything’s going great” is a red flag. At times, I’ve even seen an inverse correlation between real and self-reported progress. The more honest people are about the ups and the downs, the more I want to work with them.
YC for Writers: Our Long-Term Vision
When Write of Passage started, I was the nexus of everything. Then Will joined and took ownership over the student experience. Coming into 2022, almost everything at the company rested on our shoulders. If either of us had been hit by a bus, all that we’d built would’ve instantly evaporated.
As the company’s grown, the Write of Passage brand has developed its own reputation. Each cohort, fewer and fewer people enroll because of me. Long-term, I want the Write of Passage brand to be much larger than the David Perell one.
For inspiration, I look to what Paul Graham did with Y-Combinator. Since he founded it, the grooves of his thinking (and essays) are etched into the program’s core. But the YC brand is bigger than his now. Nobody in the program expects the majority of what they learn to come from him directly. The program revolves around principles instead of people — principles like “talk to users,” “build something people want,” and “do things that don’t scale.” Even if many of the defining principles are Graham-isms, teachable lessons can come from anybody now. Like YC, Write of Passage is more about the people you meet and the things you do than what you actually learn.
I’d like Write of Passage to be similar. My DNA will always be inside the product, but we’ll ultimately limit ourselves if I do all the teaching.
In some ways, we’ve already achieved some separation. Our Editor-in-Chief, Michael Dean now owns the curriculum. Besides being a savant at structuring and visualizing information, he teaches the craft of writing better than I ever could. We’ve also hired a lead instructor for Liftoff (named JP) who transmits the Write of Passage spirit to high schoolers more effectively than I ever could. Beyond our full-time staff, there were 38 people involved in running our most recent cohort. Every mentor program is a course inside the course, and shares a different perspective on the craft of online writing, such as publishing psychology, finding your voice, and audience growth.
We also have a team of paid editors. Students collectively wrote almost 500,000 words during our most recent cohort, and every single piece received feedback from one of our paid editors. The edits had an average turnaround time of less than 24 hours too.
Due to the power law economics of venture capital, YC disproportionately benefits from attracting A-grade talent. With our product roadmap, so will we. Our approach is different though. YC turns people into entrepreneurs; we turn them into writers. YC attracts STEM types; we attract Liberal Arts types. YC gives people a network of advisors, investors, and fellow entrepreneurs; we give people a network of teachers, editors, and fellow writers. YC measures success on revenue growth and the quality of their product; we measure it on audience growth and the quality of their writing.
The challenge now is two fold: (1) give people at path to writing well and growing their audience until they’re ready to start a business, at which point we’ll (2) pair each creator with an operator who’ll run operations at the company.
To create such an experience, Write of Passage needs to grow beyond me. I’ve never been able to run the actual company during a cohort. That was acceptable when he had one product and a team of three people. It was a nuisance when we had a team of ten people. It’ll tilt towards destruction as we grow.
Become a Better Leader
Steve Jobs didn’t enjoy the company-building process. He didn’t care about companies as abstract entities. Instead, he saw companies (so long as they had strong cultures and capable people) as the essential ingredient for building great products — what actually mattered to him. He said, “For me, it’s about the products. It’s about working together with really fun, smart, creative people and making wonderful things. It’s not about the money.”
I agree. A company is fundamentally about mobilizing a group of people in order to make an impact. When you work alone, you’re limited by your own capabilities. Groups of people are far more capable. You can make stellar progress by setting a bold vision and bringing together the right combination of talents and personalities.
Here’s what haunts me though: Every entrepreneur I’ve studied was a far better leader at the end of their career than the beginning. I’m undoubtedly the same way. I constantly ask myself: “What am I doing wrong? How can I catch my weaknesses early?” This year, I asked my entire team to critique my performance.
Multiple people felt that I was acting too impulsively. Making quick decisions is part and parcel of running a successful startup, but impulsive has a negative connotation. Some people felt that I was jumping to conclusions and changing directions on a whim. To remedy this, I’ve already started speaking in more questions and hypotheticals instead of absolutes. I’ve also been sharing more context around my decisions. Whenever possible, I try to ground them in our mission, company values, and ways of working.
As I wrote to the team: “I once again want to thank you for being radically candid with me. At Write of Passage, we care personally and challenge directly. We do it with Hearts on Fire and whenever possible, offer concrete suggestions for improvement. These performance reviews are a core part of what we do here. Thoughtful critique, clear writing, and an unquenchable thirst for improvement will continue to be rewarded here.”
Measuring the Unmeasurable
I used to be against objective metrics. I gulped the Seeing Like a State black pill too fast. You need metrics as your company scales. As a leader, your ability to distribute decision-making is one of the core constraints on your ability to grow. Setting a few clear metrics is one of the best ways to do that. Metrics aren’t the problem. Poor metrics are.
One of my biggest open questions is how to measure the unmeasurable. Sometimes, the gap between success and quality is minimal. For example, we want more than 90% of Liftoff students to enjoy the program more than their high-school writing class — while learning more too. Sometimes, it’s a little more difficult. The incentives for creating marketing content skew towards giga-cringe, lowest-common-denominator milquetoast junk. I’d sooner resign as the CEO than have our name associated with such disposable writing. How can we measure and incentivize tasteful marketing that converts?
Then, there’s the spirit of the cohorts themselves. At Write of Passage, we passionately reject the assumption that learning environments have to be boring in order to be effective. Such thinking is nonsense yet oppressively pervasive. We aren’t just fighting the education system. We’re on a crusade against the soul-numbing, brain-deadening, spirit-crushing institutional apparatus that surrounds us.
Creating magic is one way to do that. With magic tricks, what looks wondrous to the audience is predictable for the magician. It takes a meticulously planned and well-rehearsed series of steps to seemingly bend the laws of physics.
Disneyland is similar. Their magic is enabled by clear metrics and rational thinking. One of their core metrics is the percentage of customers who return for a repeat visit (they hover at around 70%). Early on, they discovered that the average person would carry a piece of trash twenty-seven feet before throwing it on the ground, which inspired the spacing between their trash cans, all of which match the section of the park where they’re located. There’s a lot we can learn from them. Rumor has it that you can take a behind-the-scenes tour to see how they run the park. It’s top of my bucket list for 2023.
Write of Passage should be a wondrous and awe-inspiring learning experience. I don’t know how to measure that though. Should we aim to quantify these emotions? If so, how should we do it? If not, how can we sustainably create magical experiences as we grow?
How Can I Write in Public While Growing the Company?
I saved the hardest section for last. This is the third time I’ve fully re-written it because I’m struggling so mightily to write consistently while running the business, especially as the team has grown.
Until 2022, I was very disciplined about my writing time. I wrote for 90 minutes every day and basically didn’t let anything get in the way. I dropped that habit, and guess what? I had an atrocious writing year. Though I didn’t miss a single Monday Musings, I only published two long-form essays during the second half of the year.
Not spending enough time in a focused writing state was the culprit, and such poor writing output is a dark cloud under an otherwise sunny year.
Part of the challenge is that I’m so new to being an executive. I feel like the kinds of Write of Passage students who are new to writing and have a lot of potential, but still struggle with every piece because they haven’t published enough. When they worry they’re not doing a good job, I say: “Relax, you’re new to the craft.”
I feel like I have the potential to become a great business leader. I really do. But I have a lot of work to do in order to get there.
Though I’m voraciously working to level up, leading Write of Passage is going to be really demanding for the first few years — and I’m up for the task. The challenging tradeoff is that I won’t have the intellectual space to write the kinds of expansive, free-flowing essays I used to write. So if I’m going to publish frequently, I’m going to have to write about what’s top of mind: building a business.
Writing is the heart and soul of my craft. Time at the keyboard is how I make intellectual progress. Most of my best opportunities come through Twitter, and the platform generates the vast majority of my email subscribers too. Once somebody becomes an email subscriber, they’re much more likely to become a long-time reader or enroll in Write of Passage.
Waking up before the birds start chirping is my only chance to write consistently again. On weekdays, I’ve found that I can only write between the hours of 6-10 (am or pm). There’s too much going on outside of these blocks. I now have a 6am standing meeting to write for a few hours each morning. Fortunately, my stamina as a writer has increased. Writing used to be such a miserable experience for me that I could only focus for 90 minutes at a time. Now, I can write for three hours, which is what I’m aiming to achieve every morning.
Whenever it’s time to write, I’ll check-in on my time tracking app: Timeular. I also use software to disable Slack, Twitter, email, and text messages while I write. Keeping my phone out of sight helps too. According to this study, the mere presence of a smartphone in your field of view can lower your brain capacity even if you’re not using it.
My goal for 2023 is to log 400 hours of focused writing time.
The decision to focus on inputs instead of outputs was inspired by Isaac Asimov. He wrote for six hours per day, and either wrote or edited 500 books and almost 100,000 letters and postcards. Though I’ll never be that prolific, I’ve taken inspiration from him.
If I write for 400 hours this year and still have an unproductive year, I’ll write about my mid-life crisis in next year’s Annual Review.