Uncharted Insider - August 2020

Uncharted Insider - August 2020

Hi everyone,

Welcome to the August edition of the Uncharted Insider.

Uncharted Update

  • Launched applications for mobile tech ventures: We launched applications for our third year of Visible Connect, an accelerator program for nonprofits changing their communities using mobile tech in partnership with Visible. Learn more about the initiative.
  • Kicking off our accelerator with Chipotle: We launched our first fully-remote accelerator for the Chipotle Aluminaries Project 2.0, a program supporting ventures that are advancing innovative solutions that empower the next generation of farmers. Learn more about the initiative.
  • 4-day workweek: We concluded our 3-month experiment on the 4-day workweek. We’re reviewing the data from the third-party evaluator and will be making a decision in the next week. Check out our most recent blog on the topic.

On taking the long view

One of our organizational values is to “take the long view,” but like many, I often find it hard to generate enough escape velocity to get above the gravitational pull of the day-to-day. A reasonable critique of my leadership of Uncharted over the last three years would be an over-indexing on decisions that optimized for short-term benefit and cash flow. But thinking/acting on a longer-term time horizon is one of those things that is more a test of courage than intellect, more an exercise in discipline than vision. And I’m quite driven to grow in my ability to do things that require courage and discipline, especially when the benefits of taking the long view are so numerous, as this article* suggests. It makes a few key points:

  • So few people are operating on long-term time horizons that doing so elevates you into a realm where you find less competition.
  • Time horizons are one of the most under-considered factors that dictate decision-making, and the analyses of a decision change when the time horizon changes (see this cartoon).
  • The power of compound interest means that daily actions in service of long-term goals have exponential impact. There are few investments that yield as extraordinary a return as an investment in our own deep, long-term learning.

*The patriarchal, gendered nature of this article is not lost on me: not only are the article’s subjects themselves privileged men, but presumably so is its author, and many of the suggestions outlined therein are only possible to those with such gender-race-class privilege. Nevertheless, some good points remain.

On radical ideas

One of my meta-learnings from 2020 is how fast things can move from being perceived as impossible to being perceived as inevitable. We’ve seen it with government bailouts, societal behavior, and public perception of social movements (like Black Lives Matter). Progress happens in leaps; what was once considered radical and fringe can quickly become mainstream. The ever-shifting spectrum of what’s perceived to be “mainstream” is called the Overton Window, a window of policies perceived to be politically acceptable. Outside the window, there are those policies that are considered increasingly radical and unthinkable. (The Overton Window concerns itself with policies, but the concept is relevant to ideas, technologies, business models, and movements.) 2020 is a lesson is how quickly the Overton Window can expand and shift, and it has me thinking about three questions:

  • Are there certain characteristics that radical ideas, policies, and approaches inherently have that increase the chances they will go mainstream?
  • What surrounding pre-conditions exist that signal a radical idea is at a tipping point?
  • What helps accelerate the transition from radical to mainstream?

The word “radical” is fraught with negative connotations, but its definition, I recently learned, is “of, relating to, or proceeding from a root.” For those of us interested in addressing root causes of social problems and for those us dedicated to operating in the uncharted territory outside of the Overton Window, an emerging curiosity for us as an organization is this question: how can we help to mainstream the radical?

Can you help?

  • We are looking for connections at the following organizations to explore a new initiative we’re launching focused on closing wealth gaps in the US. If you’re able to make a connection, I can share more context.
  • Paypal
  • Bloomberg Beta
  • Dalio Philanthropies
  • Inherent Foundation
  • Woodcock Foundation
  • We're looking for a pro bono lawyer that can spend 2-3 hours reviewing our venture grant agreements / grant reporting to ensure we're legally compliant as we begin providing more grant funding to for-profit and 501c4 organizations (Note: we are a 501c3 ourselves). Know anyone who can help?

What I am reading

Something personal

I’ve spent a number of weekends this summer in the forests of our Colorado mountains, hiking about, reading poetry, and thinking about the Milky Way. Maybe it’s been the looming fear of our own mortality with COVID, or perhaps it is the way things have a habit of showing up everywhere once you’ve just discovered them somewhere, but I began to regularly see fallen pine trees who were gently releasing themselves back into the soil, nestling into the forest mulch like a skeletal shipwreck becoming part of the seabed itself. They were transmuting themselves from dead into alive, from tree into soil, from vertical into horizontal as they crumbled and decayed into hundreds of richly-colored caramel pieces of wood until only the long, stretching silhouette of the trunk remained, a faint outline of what once was, and what will be again. Trees are so brave in how still they stand when the storms come, so patient in their faith that a flowering spring follows every denuding winter, and so dignified in their surrendering back into the earth when they know it’s their time.


With patience and vigor,