An account of one of the most exhausting and exhilarating months I can remember

💌 The Roundup // 013

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On the evening of March 24th, Ash and I FaceTimed my parents to share that we were days away from boarding a plane to Washington D.C. At any other time, the news might have seemed mundane. But in the midst of this Coronavirus outbreak, my mom’s usually stoic face flushed with worry. “Why are you doing this?” she asked, her voice quavering.

It had been almost exactly a month since I first realized Coronavirus was going to be a big deal. I remember the day because I panic-ordered masks and hand-sanitizer from Amazon and told my parents to stock up on frozen food. Over the next two and a half weeks, Ash and I began social distancing. We stopped hosting friends, working out of coffee shops, or eating at restaurants. Being cooped up at home and in between jobs, I found myself with lots of free time. While I generally try to be disciplined about social media usage, I couldn’t help logging into Twitter every ten minutes to read the latest headline or hot take about COVID–19. 

The more news I consumed, the more frustrated I felt about how our country was handling the crisis. Culture warriors squabbled, reporters downplayed serious risks, and politicians encouraged people to continue their normal routines. I felt addicted to the news cycle but powerless to impact it.

On March 14th, I got a call from my friends Rachel and David Romer Carlson. Like many recent conversations, it started with us lamenting how no one seemed to be taking this seriously. “They’re still planning to throw a huge concert in Denver this weekend,” said David. Eyes wide, I shook my head. “We need to do something,” said Rachel. “Do you want to help us out?”

I paused, struggling to imagine what ordinary citizens could do to prevent this coming train-wreck. Weren’t there people more qualified than us who were supposed to be solving this? But as the Twitter feed of the past few weeks scrolled through my head, I realized this was the first time in weeks that I’d heard anyone sound like a leader. “Sure,” I said. “I’m in.”

Within a day, we spun up a team and gathered signatures from over 300 CEOs who committed to a set of proposals authored by our newly formed organization, Stop The Spread. Inspired by watching my friends step up to fill this leadership vacuum, I began devoting more time to volunteering with the organization. While the hours were long, and the work was outside of my domain of expertise, I finally felt the energy and clarity of focus I had been craving.

As we learned about the looming shortages of ventilators and PPE and the coming strain on our healthcare system, we saw an opportunity to rally the business community to help. Several members of the team flew to Washington D.C. to help coordinate the private sector’s efforts at the federal level.

The folks in DC started spending their days meeting government officials to advocate for companies that wanted to help fill critical supply shortages. The stakes were getting higher and the work more impactful, but, as the center of gravity shifted to DC, I was finding it harder to keep up from San Francisco. 

This came to a head on March 24th. I woke up after getting very little sleep. That day, the team was in and out of meetings, and despite everyone’s best efforts, I found I couldn’t get the information I needed to contribute effectively. I ended the day feeling frustrated. 

Sensing my mood, Ash asked what I wanted to do. I knew the team had too much urgent work to devote energy to establishing remote working best practices, but, if things kept going this way, I wasn’t going to make the impact I wanted. “I think I have two options,” I said. “I can either scale back my commitment, or I can go out there and join them.” I looked at her, anticipating a worried reaction to my latter suggestion. “What if I went with you?” she asked. I smiled, reassured, once again, that I married the right person.

Realizing the implications of getting on a plane at a time like this, Ash and I wondered whether we were acting irresponsibly. We had been religious about sheltering in place and protecting ourselves when we went out. What was all that precaution for if we were going to put ourselves at risk? As we stepped outside to take a walk, we talked about our parents and grandparents. They were the ones who were truly at risk. If relatively young and healthy people weren’t willing to run into this fire, who would?

I also thought about my dad and all the amazing stories he collected in his life – like the time he almost got kidnapped in Mexico City, or when he resigned from the Nixon administration after being asked to make speeches defending Watergate. Listening to those stories as a kid, I always hoped that I’d have a few of my own to share with my kids someday.

That evening, as we FaceTimed with my parents, those were some of the reasons we gave to my worried mother about why we had decided to buy one-way plane tickets to D.C. 

Our week in D.C. was surreal. Working out of a pair of conference rooms in the nearly empty JW Marriott hotel, we spent our days and nights coordinating with business leaders and government officials about how to respond to a growing crisis that no one was prepared for. Each time we walked through the hotel lobby, we would pass screens with news anchors reporting on the growing medical supply shortages we were trying to help solve. Despite the long days, it never felt like enough time, knowing as we did that every hour without a solution meant lives were being put at risk.

While the enormity of the problem has felt overwhelming, there has been something magic about collaborating with people who are all devoted to a common mission. Working alongside longtime friends like Aidan, Alex, David, Hamish, Harris, Rachel, Ryan, and Shannon has given me the exciting opportunity to see the full potential of their abilities. I’ve also gotten the chance to spend time with new and talented teammates who I hope to work with on future endeavors in the years to come.

Many of us have felt inspired by the private-sector leaders, like those at Brooks Brothers, GM, and Ventec, who have taken risks to retool their production lines in service of our country. Everyone’s shared concern for this problem has allowed these efforts to materialize much faster than normal. High-level people answer emails, meetings are set up quickly, and status games diminish in importance. The closest thing I can compare it to is the feeling I used to get watching episodes of The West Wing.

Given the visibility of this challenge in the news cycle and our belief that Stop The Spread should not take center stage, I can’t share all the details of my experience. That said, I’m proud of the work our team has done so far. And this is just the beginning. We’re working with lots of other amazing partners to catalyze their efforts to solve America’s critical supply shortages of ventilators and PPE. Despite the inaction of many of our institutions, I remain encouraged by the many newer leaders emerging to respond to the urgency of this moment.

While it is easy to view COVID as a freak event, the fact that it has escalated into a global crisis should signal to us that this pandemic is merely a symptom of a much larger problem. The institutions that served us well in the decades after WWII are no longer suitable for the challenges of the day. To prevent more crises like this, we need people to step up and rebuild the systems upon which humanity depends. 

These new institutions cannot be created by the same people who built the previous ones. It’s time for a new generation to take the wheel. This will require Millenials to grow out of our prolonged adolescence. We can no longer afford to be a group of keyboard commentators on the state of the world. We need to divert our energies from seeming virtuous to the much harder task of being virtuous.

I am not suggesting everyone follow Ash and my somewhat irresponsible example of boarding a plane for D.C. Instead, I’m simply hoping to motivate you to step up and fix the broken institutions that surround us. Whatever domain you operate in, whether its academia, business, medicine, law or local government, there are systems around you that need fixing. Don’t wait for the adults to show up and give you permission. Seize this opportunity and take your turn to shape the future.


🏫 Can a School Have Product-Market Fit?

(7-minute read from Brian Tobal)

I typically avoid writing about the immersive education (aka bootcamp) space since it seems a bit inside baseball. My general view is that most of these schools spend too much time telling students things they want to hear (“We have a 95% placement rate!” or “You’ll double your salary!”) and not enough time telling them what they need to hear (“No one can place you into a job.” or “Entry-level employees that get paid too much risk getting fired”). That said, this article from the Head of Academics at Flatiron School (which, from what I’ve heard, is a great program) raises a bunch of great points about what makes schools successful:

  1. Schools can only justify charging high prices if they provide their students with a valuable signal in the hiring market

  2. Selective admissions enable better student outcomes

  3. Unselective admissions can burn out staff and turn off hiring managers

  4. Scale makes it much harder for schools to be selective

  5. Just because a school has developed a format that prepares students well for one career (e.g., software engineering), doesn’t mean the same format will be well-suited to an adjacent career (e.g., product design, data science, etc.).

A few related points that I’d add:

  • Selective admissions help schools build positive network effects within student cohorts as well as in the greater alumni community.

  • Positive network effects can have a significant impact on student outcomes

  • Unselective admissions can create negative network effects

  • If students don’t form bonds with one another (due to distance, perceived status differences, etc.), staff get over-burdened with student questions and stress

  • Good staff members are hard to keep, as they have many options. Allowing them to become overburdened by students will motivate them to leave

  • It’s much easier to help students when they are employed, and thus not in survival mode

If this is a topic of interest to you all, I’m happy to discuss more in future issues of the newsletter.

🌳 How to Retain Talent — and How to Lose People the Right Way

(5-minute read from Niko Canner)

Few of us, if any, are currently working for the last organization that will ever employ us. Yet, a majority of HR departments view each employee departure as a mark against their company’s retention goals. There is a more enlightened way to view these breakups.

When an employee leaves, a company should consider whether they took the time to understand the employee’s career goals and attempted to provide appropriate opportunities for directional growth. Niko Canner used this concept to help develop a series of post-mortem questions called “the retention tree:”

  1. Did we have an open dialogue with that individual about their dreams, priorities and concerns, the different kinds of opportunities they were thinking about on the outside, and what might be possible for them within the firm?

  1. Did we think creatively and well about the best way for that individual to realize their aspirations within the firm, and identify specific things that would make a positive difference?

  1. If we made any commitments based on this dialogue, did we fulfill them?

While asking these questions won’t prevent every departure, it will encourage managers to have the right conversations with direct reports so that the company won’t be blindsided when its employees decide it’s time to move on.

Routines & Avoiding Stupidity

(10-minute listen from James Beshara)

James Beshara recently highlighted a mental model about decision making that’s changed the way I think about my daily routine. The idea seems to have originated from investor, Adam Robinson, who defines stupidity as:

Overlooking or dismissing conspicuously crucial information.

He goes on to list seven factors that lead to this state of mind:

  1. Being outside of your typical environment

  2. Changing your routines

  3. Being in the presence of a group

  4. Being in the presence of an expert

  5. Doing any task that requires intense focus and not being in an environment that allows for it

  6. Information overload

  7. Physical or emotional stress

As someone who uses novelty to spark creativity, I’ve always tried to vary my routines and environments. But this framework has changed my thinking. I’m now making an effort to delineate between creative and execution-oriented routines. For the former, I’m still trying to vary my environmental cues. But, when making important decisions, I’m attempting to schedule them into routines that stay relatively consistent.

🧟‍♂️ A Survive/Thrive Theory of the Political Spectrum

(15-minute read from Scott Alexander)

Watching the world wake up to the threat of Coronavirus over the past month, I can’t help think of Scott Alexander’s classic Survive/Thrive theory of the political spectrum. To summarize his hypothesis:

Rightism is what happens when you’re optimizing for surviving an unsafe environment, leftism is what happens when you’re optimized for thriving in a safe environment.

As our environment becomes increasingly hazardous, it’s worth understanding the survival impulse that defines rightism. Instead of tuning into Fox News or CPAC, Alexander suggests we imagine landing in the middle of a long-term Zombie Apocalypse. In that kind of scenario, how might our values change? We would probably want:

  • Guns and lots of them

  • A strong military or police presence

  • To be surrounded by people with practical skills (no room for comp lit majors unless they can operate a shotgun)

  • The ability to prevent outsiders from joining our group (until they prove themselves)

  • Hierarchy and conformity to maximize group coherence

  • The ability to freely maximize wealth to acquire resources

In other words, “take actions that would be beneficial to survival in case of a zombie apocalypse” seems to get us rightist positions on a lot of issues. We can generalize from zombie apocalypses to any desperate conditions in which you’re not sure that you’re going to make it and need to succeed at any cost.

I believe individuals and societies should gravitate toward whatever political philosophy helps them meet the challenges of the day. When times are good, we need guidance about how to divvy up the bounty, while in times of struggle, we need a belief system that will protect us against the elements. 

👓 Reality Without Frameworks

(4-minute read from Cedric Chin)

Long-time readers can attest to my affection for strategy frameworks. Whether it’s a 2x2 matrix or a systems-diagram, frameworks can serve as useful tools to simplify the messiness of reality. The problem with relying too much on them is that your perspective on reality can become oversimplified.

Your ability to make sense of your unique situation is titrated through the framework’s model of reality. The more you rely on frameworks, the more you lose your ability to think from first principles.

If you find yourself falling into this trap, spend more time gathering data and less time interpreting it. Resist the temptation to fit your observations into a framework, and instead sit for a while with the uncomfortable contradictions. You’ll be a better thinker for it.


*Header image credit: Alicja Colon