Uncharted Insider - September 2021

On the humility of counterfactuals, the problems with framing the problem, and how we've never been taught to eat.

Uncharted Insider - September 2021

Hi everyone,

Welcome to the September 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.

Uncharted Update

  • We kicked off our Economic Inequality Initiative and announced our cohort of 10 ventures. Meet our cohort here.
  • We are hiring for an Operations Associate. Who is the early-career person in your network who is passionate about operations and company-building and has world-class organization skills? Spread the word.

On the Humility of Counterfactuals

In the wake of the American withdrawal from Afghanistan, it seemed as though everyone instantly became a foreign policy strategist with a hot-take on what should have happened (nothing springs into action quite like the dogma of an armchair expert). Largely missing from the cacophony of opinions was an earnest exploration of counterfactuals, which would have considered how the consequences might be different had the US chosen a different path. Counterfactual thinking is merely a thought-experiment, but its virtue as an intellectual pursuit lies not in its predictive accuracy, but rather in the way it brings us into relationship with the possibility of alternatives. The grip on our convictions begins to loosen when we observe the role-play of an alternative sequence of events and when we entertain its infinite consequences. Decision-making research points out that widening the frame to explore more alternatives leads to better decisions, but perhaps the greatest prescription for counterfactuals is not in the science of decision-making, but rather in treating our tendency to be intellectually overconfident about what is right. Simply giving ourselves the space to remember the existence of counterfactuals is enough to soften our convictions and expand our curiosity.

On Framing the Problem

Not enough attention is paid to how we frame and approach problems. I’ve seen two common mistakes:

1. We don’t frame the problem well

Entrepreneurs often make the mistake of framing the problem they’re tackling too broadly because they feel pressure for their work to be grandiose and panacean. In saying they are “solving climate change” or “effecting systems-change” or “eliminating [insert bad thing],” they mistake the mission they're on with the problem they're solving. There are risks with being stuck at too high a level of problem-framing: it leads to a thin understanding of the actual problem, an unclear relationship between solution and problem, and a poor use of metrics to measure progress. Better framing leads to more specific problems which leads to more pinpointed solutions.

2. We match the wrong solution with the problem

There are times when I've been surprised by the disconnect between the stated problem and an entrepreneur's proposed solution (you're trying to solve a systems change problem with an app? You think this financial literacy course can create financial freedom for people making a minimum wage?) This tendency to mismatch problem and solution might suggest ignorance, naivete, or hubris, but it could also mean that entrepreneurs simply are choosing the solutions they’re already most familiar with. What kind of economic justice solution should we expect from someone who has built a career teaching financial literacy? What kind of systems-change approach should we expect from someone who is an app developer? What kind of solution to homelessness should we expect from a VC who has invested in technology startups? For the person who has been trained to wield a hammer, it’s easy to believe that every problem is full of nails needing to be hammered.

We often advise our entrepreneurs to “fall in love and start with the problem," but the best predictor of the type of solution that someone will come up with is the type of solution they are already most familiar with. Maybe they’re falling in love with the problem, but they’ve already chosen their solution. Therefore, we have two options:

  1. Start with the solution and back into the problem: Instead of starting with the problem, we start with the solution-set we are most skilled at and go hunting for a problem until we find a match. This is an asset-based approach. Double down on what you’re good at. Stick to your lane and be willing to frame problems at a narrow, specific level.
  2. Start with the problem but be ready for an existential flex: Chase the problem until it demands that you reinvent yourself (an example here is Netflix transforming itself from a DVD delivery business to an online streaming one). This is a market-based approach where you let the market mold you. The risk here is that you might not be the best person or you might be lacking the skills to truly solve the problem. Humility is needed.

Too many entrepreneurs don't have the courage or the honesty to choose one of these options: they either force their solution onto a problem, or they aren't willing to accept that the problem requires them to let go of their existing theories and be transformed.

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? One of the most powerful ways we can learn is by 1) gleaning the insights from those around us, and then 2) compounding those learnings over time. 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.

From Bryant Mason, organic farmer in Paonia, Colorado and Founder/CEO of Soil Doctor.

How often is sustainable grazing a red herring in the Regenerative Agriculture movement? Many people tout that "cows are a solution to climate change", which is counterintuitive yet alluring. But the underlying assumption is that cows must be managed extremely well in order for carbon sequestration to occur. I see a lot of cows in Western Colorado and not a lot of holistic management. Visiting the best grazing operations in my area has made it clear to me that grazing to regenerate soils requires more time moving animals and more acreage to rotate them on, two barriers for many producers. There's a deep human component too. Like anything in agriculture, what is good for the land is always site-specific and requires an attentive and well-trained human steward. There are a handful of inspiring examples that are well-circulated. Yet I wonder if the mere promise of regenerative grazing leads us to collectively justify animal agriculture carte blanche without actually addressing dietary changes (i.e. people eating way less meat).

Can you help?

  • Do you know of someone who would like to fund early-stage solutions to economic inequality? We're looking to expand our funder pool in 2022.
  • Do you know Noorain Khan at the Ford Foundation?
  • Do you know Jessi Shikman at First Round Review or anyone at First Round who might be able to connect us to Jessi or folks on the First Round Review team?
  • Do you know our next Operations Associate?

What I am reading

  • How climate change will affect every county in the US. A fascinating report by ProPublica where you can enter your county and evaluate its long-term viability in a warmer, dryer, and more unpredictable world. Here.
  • One of the most underrated differences between groups in the US is the difference between those who understand exponential growth and those who do not. We’ve entered an exponential age, but we’re thinking linearly. Here.
  • From 2014 to 2019, Hispanics saw a faster growth in income than any other major demographic group in the US, and in the past two years, Latino-owned businesses have grown at an average rate of 25%, compared to White-owned businesses at 19%. If the US Latino market was its own country, it would be the 8th-largest economy in the world. Happy Latino Heritage Month!
  • In the next 25 years, tackling major social issues will require the more proactive guiding of markets towards equitable outcomes than the reactive fixing of markets. Supply-side innovation will be more important than demand-side fixing. What the progressive left misses in their obsession to fix problems. Here.
  • Book: Empire of Pain: The history of the Opioid epidemic and the rise of the Sackler family. A disturbing portrait of a family addicted to its own wealth, living in an alternative world, and protected by all the securities afforded to the wealthiest Americans.

What I am writing

I am expanding my writing beyond this monthly Uncharted Insider by writing additional posts and reflections here on my Ghost site (it’s similar to Substack). Here are a few things I’ve written in the last month:

  • I’ve taken three full weeks off from work this year to go on deep learning retreats, and I wrote a guide for those interested in designing and structuring their own deep learning retreats. Here.
  • First principles thinking is all the rage now. But what actually is thinking by first principles? I wrote a primer on the concept here.
  • The bravery of first days and how organizations are nothing more than the daily choices of its staff to keep showing up and doing the work. Without the daily choice made again and again, an organization ceases to exist. Here.

Something personal

Last month I shared about the 2-week bootcamp I attended at a culinary school in Vancouver on the principles of plant-based cooking. Each day, we would learn to cook a range of new dishes, which we then plated and ate during mealtime breaks. The students in this course were eager learners in every respect, and we all worked with alacrity to make each dish delicious and beautiful, but when it came time to eat what we had created, so many students would mindlessly eat their hard-earned culinary creations while scrolling on their phone. I did this a few times myself until I realized what I was doing: I was attending a cooking school to learn how to cook, only to completely miss the opportunity to savor and learn.

This revelation occurred to me one day after I had mustered the courage to approach one of my instructors and offer a confession of the highest culinary sacrilege: that I have a poor sense of taste. He dismissed my secret as little more than being out of practice, instead choosing to ask me me how quickly I eat (quickly) and if I often eat while doing other things (often) and if I have ever slowed my tasting enough to notice the small notes of rosemary in a large stew or the ephemeral tang of citrus in a mole sauce (rarely).

What is the point of cooking if we regard the entire endeavor as nothing more than the utilitarian act of nutrient transport into our bodies? If our food is a means to an end, it is not worth the trouble to constantly tend to a pot of risotto, stirring and testing and nursing it until it reaches its pinnacle of flavor and thickness. This extends beyond the kitchen: we are not paying attention. We are disembodied eaters and mindless consumers in a world blooming with flavor.


As always I welcome your feedback and ideas.

Denver for a while,