My Liberalism 2.0 Fellowship Application


Some context before you read


This document contains my unedited application for a Liberalism 2.0 Fellowship via Emergent Ventures. I was not selected.

However, the program’s facilitator, Tyler Cowen, suggested I consider turning this project into a business and re-apply for an Emergent Ventures grant, which I was later awarded. You can find my unedited application for that here.

My application


Hello, hello! I hope all is well!  I’m writing (at the nudge of Tammy Winter[0]) to apply for a Liberalism 2.0 Fellowship.

Over the last 9 months, I have been (mostly quietly) working on The Kool-Aid Factory, guides for ambitious organizations on shaping company culture.

Company Culture is simply how a company gets the work done and every organization has their own flavor. The Kool-Aid Factory is a series of zines about creating, and recreating, the recipe together. The zines are targeted at leaders, managers, and operators at ambitious organizations and will live online as free, easily-printable zines (see Wizard Zines by Julia Evans) as an example. The name is a somewhat cheeky attempt to reclaim the chide, “drinking the Kool-Aid,” oft-deployed at overzealous tech employees.

The project is based on an insight that at most forward-thinking companies, culture is considered a first-class priority but is not treated as a first-class product. Sure there’s organizational design and the MBA curricula, but culture is an underutilized mechanism for driving a business forward. I believe there is a very real opportunity to put forth a tactical playbook for crafting a company culture that reinforces business goals and I am ~60% of the way through writing one.

The Kool-Aid Factory embraces the kaizen philosophy that continuous improvement of a system is everyone’s responsibility and happens by way of both local and systemic changes. So, the goal is that, at minimum engagement, anyone who stumbles across a zine should have a blast reading a few sections and come away with concrete ways they can positively contribute to their company’s culture now. At maximum engagement, the full set of zines is designed as a set of building blocks for creating a company culture that enables employees to work at their fullest potential and satisfaction while servicing the collective goals of the company.

The tactics will be accompanied by stories of how other (mostly tech) organizations have put them into practice (see collection of some examples here) and wherever relevant, there will also be templates that lower the barrier to getting started (like this checklist for company docs to read for onboarding, or this one for experimenting with MadLibs for a fun team kickoff).  

If you want to take a look for yourself, the very work-in-progress material can be found here).

Pique your interest? There’s more.


What this project has to do with “liberty, prosperity, progress, and the foundations of a free society”

There have been and always will be efforts that bring ambitious people together to achieve ambitious goals. We all have our favorites; Manhattan Project, NASA during the space race, Bell Labs, Pixar, Apple, Tesla, the list goes on. When the stories of these organizations are told, team culture is always cited as a critical success factor but it’s often described as some magical combination of forces that can only be articulated once it’s already in place.

In reality, though, whether intentionally or not, culture is created through an ongoing series of actions. So it stands that culture can be prescribed a priori (not just described post-hoc). The Kool-Aid Factory shows leaders, managers, and operators how.

If the tactics The Kool-Aid Factory advocates for are widely adopted, I think we will see meaningful ripples in progress and prosperity at both the company and individual level. My hope is that by sharing clearly-articulated, bite-sized, implementable concepts, ambitious companies, and the people that comprise them, will be able to make more efficient progress towards realizing their ambition. Even if the ideas are merely explored at an intellectual level, I think we can elevate the discourse about the value and craft of company culture-building such that even better ideas emerge over time.

The Kool-Aid Factory is undoubtedly a creative interpretation of your topic requirements, but I’d imagine that many impactful ideas that cut across are.

How I came to this project

When I joined Stripe in March of 2015, I was blown away by the employee onboarding process; specifically, how much content was dedicated to expectations for an employee’s contribution to company culture. Before joining Stripe, I had worked at several other tech companies of various shapes and sizes (from a six-person YC-funded startup to Google), and it was unlike anything I had seen before.

At that time, Stripe’s headcount had recently crossed Dunbar’s Number and I concluded that Stripe’s leadership team was taking the task of maintaining the Stripe hivemind very, very seriously.

I’d heard the trope before that company culture was up to everyone to build, but Stripe’s documentation showed us specifically *how* to do that. The source of it all was a set of (extremely well-written) operating principles. They acted as an implicit contract between the company, employees, and each other that stated “this is how I will strive to act when I am working with you,” “I want you to act this way with me when you are working with me” and “when I lose sight of these values, please remind me. I will do the same for you.” This manifested in all sorts of interesting ways; some leader-driven, but many employee-driven. Over my subsequent half-a-decade working at Stripe, the company 10x’ed in size and the value of the relentless focus on principled culture-building revealed itself over and over again.

This observation set into motion diligent note-taking on Stripe organization and an obsession with reading and talking about how company cultures come to life. I’ve slurped up over 1000 books, podcasts, and essays on the topic and have talked to dozens of friends/colleagues about manifestations of culture in their companies[1]. This obsession was bolstered through my work standing up Stripe Press (including publishing its first six books and acquiring 4 more to-be-published) and talking to writers and readers.

My experience and “research” (though I wouldn’t have called it that at the time) led me to the insight I cited earlier: company culture is considered a first-class company priority, but not treated as a first-class company product.

As a result, there isn’t much good, tactical writing about the craft of company culture-building on the ground-level. So, over the 2019 end-of-year holiday, I feverishly started writing to fill the gaps I saw and haven’t stopped since.


More research, more insights

As I’ve bounced early ideas off others, researched and written more, and spent a full year at another wonderful company that does not have the same relentless focus on culture, I’ve come to a few more conclusions:

  • Culture doesn’t happen to companies and it’s not just the sum of the parts. It can be designed and executed upon with intentionality
  • Companies with strong cultures do better work, and the process of doing the work is more fulfilling for everyone 
  • There is appetite for this material (one public example is this somewhat viral tweet I wrote about the Stripe magic)
  • Companies are mostly comprised of individual contributors, but operating is not treated as a craft in the way managing, leading, or founding is.
  • Interest in operators is bubbling up (see The Renaissance Collective community, Delian Asparouhov’s podcast about operators, etc.)

The output of this project took various forms (a series of blog posts called “surviving the org”, a book called “the principal operator,” an advice column, features on great operators, reviving my old “so many rootlets” blog about being a human and an employee, but I settled on The Kool-Aid Factory zines as the final format about three months ago.


Why a zine?

My time working on Stripe Press taught me how important the artifact of the work can be to the content of the work. Even your favorite article doesn’t end up on your coffee table or desk! It feels different to hand over a thing than send something over an email. A strong visual identity, thoughtfully crafted, brings another dimension of intentionality and depth to the project.

It was important to me, for example, that the content I was working on did not feel heavy or dense to consume.

The zine felt like the perfect fit. The format is designed for maximum snackability and shareability. They have a strong visual identity and embrace a do-it-yourself philosophy. They’re a great bridge for philosophical ideas and ground-level behavior. They’ve historically been deployed by renegades to influence culture in a somewhat playful format; it’s the perfect metaphor for ambitious techies with a knack for (ideally thoughtful) “disruption.”

Of course, the project will also have all content available for free on the internet so anyone can access it from anywhere. They’ll be released in issues. Atlanta-based graphic artist and storyteller, Leila Register, is helping me bring the work to its full visual expression and here is the moodboard we’re working off of.

Looking to learn even more? I am here for questions, thoughts, feedback, or always to say hi.


[0] She’s the kind of friend who gets you to aim the telescope a bit higher, isn’t she? I’ve benefited from quite a few of those in recent history, present company included.
[1] I plan to open this spreadsheet up and allow anyone to add traditions from their company