Uncharted Insider - May 2021

The collapsing of categories, unbundling and rebundling, and deep learning retreats.

Uncharted Insider - May 2021

Hi everyone,

Welcome to the May edition of the Uncharted Insider. Do you know someone who would enjoy the Uncharted Insider? Forward this email to them and they can subscribe here.

As a quick note, this Uncharted Insider won’t change (I like that it's an actual email and not a glossy newsletter), but I am also experimenting with reposting this content on banks benitez.ghost.io, which is an online writing platform I’m exploring.

Uncharted Update

  • Recruiting agriculture ventures: We are looking for ventures who are reimagining the US food system for our accelerator with Chipotle. Applications close in 5 days.
  • Who is the best ag-tech or future-of-agriculture entrepreneur you know?
  • Recruiting economic inequality ventures: We have opened applications for our Economic Inequality Initiative, and we’re looking for early-stage social entrepreneurs, movement builders, and nonprofit innovators who are tackling wealth inequality in the U.S.
  • Who is the best entrepreneur or activist you know working on this issue?
  • We’re hiring for three roles, and we’ll pay you $500 if we hire someone you refer
  • Director of Economic Inequality ($90 - $100k)
  • Who is the best former entrepreneur you know looking to coach and scale other entrepreneurs working on economic inequality?
  • Program Manager ($60k - $75k)
  • Who is the best program manager you know who has experience working with social entrepreneurs?
  • Program Associate ($50 - $55k)
  • Who is the most organized project manager you know?

On the collapsing of categories
Tressie Cottom,* the American intellectual who writes about inequality and status, said recently on a podcast that Americans are being forced to "rethink almost every meaningful category that we’ve kind of taken for granted," and this amounts to a grand moral panic of our time. Categories that once felt ironclad are being revisited and deconstructed. To list a few examples: gender is not a binary, but is on a spectrum. Racial groups are something we invented out of thin air, but also a very real organizer of society, caste, and culture. Our individualism is undeniable, but so is the fact that individuals create social groups and those groups wield power. We like to think that we're rational creatures, but there are unconscious biases that operate below the surface of our reason, invisible even to us. We don't live in a meritocracy, but the relationship between input and output still matters immensely to our sense of fairness and our economic mobility. We're complicit in systems we didn't invent, but perpetuate simply through living the easiest, most default versions of our lives.

The point Cottom goes on to make is that we're entirely ill-equipped to navigate this period because we're having the most complex, nuanced conversations on the most un-nuanced and histrionic mediums of social media. It's like we're using large blunt-force farm implements to do delicate woodworking, or as Cottom says we're having "thick conversations in thin spaces." It might be tempting to chime in and add our slice of wisdom to these thick conversations, but I wonder if the work of cultural and organizational leadership is actually to focus on thickening the spaces instead of contributing to the topics. We're missing spaces, not ideas. We're missing bravery, not brilliance. We're missing listening, not thought leadership. We are too focused on the content of the conversations and not spending nearly enough time creating the spaces where we can explore them. But, we might be tempted to stop there and simply hold the space, entertain the conversation, and ultimately become paralyzed with no way forward. Leadership, ultimately, is more about the movement through ambiguity than a love of it.

*I referenced Cottom's podcast with Ezra Klein in last month's Insider as well because it is one of the most thought-provoking pieces of content I've engaged with in the last year, and Cottom is a genius on the thickest conversations of our time.

On unbundling and rebundling
We're living in an age of things being unbundled and rebundled by the internet. Take the idea of community; in the former bundle, people were closely connected to those with whom they were in physical proximity. In the new bundle, we might not know the neighbor who lives next door, but we're deeply connected to online communities of people all over the world who share a common interest. Social media is unbundling us from our proximate communities and rebundling us into likeminded, digital ones. There are other examples:

  • Old bundle: Records and CDs.
  • New bundle: Spotify and now NFTs

Higher Education:

  • Old bundle: 4-year degrees at prestigious universities on residential campuses
  • New bundle: Free online courses, coding academies, education by Zoom

Journalism (many different bundles and rebundles here):

  • Old bundle: professional journalists working under major mastheads
  • New bundle: citizen journalists with smart phones and cameras


  • Old bundle: fiat currencies for each country and currency exchanges between countries
  • New bundle: global cryptocurrencies

Once I learned about this idea on this podcast with Balaji Srinivasan (a lengthy but outstanding listen), I started to see the pattern of unbundling-to-rebundling everywhere, and it has me thinking about the opportunities and threats this trend poses to major social change in the US. One example is portable benefits. In the old bundle, healthcare is tied to employment. In the new bundle, our benefits might travel with us, independent of a job. What examples of unbundling-to-rebundling are you seeing, and what are the threats and opportunities?

Compound Insight
What big trends are you seeing? What insights have you had? What are some major learnings in the last month in your work? I announced a new section to the Uncharted Insider last month called Compound Insight, which shares key learnings, patterns, trends, or insights from the community of readers of this monthly letter. Simply share any big ideas or learning using this link, and I’ll select a few to publish in the next Insider so this community can continue to compound learnings from each other.
This month: Kristi Petrie, Executive Director of the AJL Foundation poses the question: "Is there opportunity for reparations through crypto currency?"

Can you help?

  • What family foundations do you know who are focused on economic inequality, domestic poverty, and economic mobility? We want to connect with them!
  • Can you give us one piece of feedback to make the attached 3-pager better?
  • See above for recruiting ventures for our ag-tech accelerator with Chipotle and our economic inequality accelerator
  • See above to help us hire three new roles (we will pay you $500!)

What I am reading

  • 29% of young Black Americans became first-time investors in 2020, compared to 16% of white Americans. How Robinhood and other retail trading apps are closing the wealth gap. Here. Plus the backstory on Robinhood's questionable practices and history.
  • Is Mars ours? What we need to learn when thinking about colonizing other planets. Lessons from our own failures at manifest destiny.
  • The coming demise of oil and gas and predictions of what the next wave of green innovation will do, based on the history of new ideas. Here.
  • Our complicated relationship with Native Americans and national parks. How "America has succeeded in becoming more Indian over the past 245 years rather than the other way around." Here.

Something personal
Every year, two of my best friends and I take a stand-up paddle-board trip down a river in Utah. This year's trip was scheduled for late April, but at the last minute as we were driving to our put-in, one of my friend's wives had a health scare, so we cancelled the trip and turned the cars around (all is well with her now). In the span of an hour, I suddenly had eight days with no plans, which, as a person who is governed by his brimming calendar, has never happened before. I had blocked the time off and requested vacation days, so I decided I wouldn't just go back to work. Instead, I kept my email autoresponder on, and chose to turn the week into a solo retreat focused on deep (non-Uncharted-related) learning.

I found a small Airbnb in the desert outside of Taos, New Mexico and built out a specific learning agenda for my time. I spent the time in deep learning mode: synthesizing learnings from books I've read into notes and summaries, taking two online courses, listening to podcasts by futurists, developing a memo on first-principles thinking, reading poetry, and walking the dirt road outside my cabin, inhaling and exhaling in slow, pensive rhythm. Initially, I was disappointed about the change in plans (I love river trips), but this deep learning retreat was one of the best things I have ever done. I learned more, wrote more, and produced more creative work in one week than I have in 6 months. If you've done a deep learning retreat, I'd love to hear about it.