The Insider - October 2023

On my next professional chapter, the game of leadership, and the courageous middle ground

The Insider - October 2023
Photo by Sekwang Chia / Unsplash

Hi everyone,

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

On my next professional chapter

After 18 months on the Ezra Climate team, I am resigning so I can carve out time to determine my next professional step. I love the Ezra team and have become a believer in Ezra’s work to accelerate the decarbonization of our world by leveraging fintech tools and financial vehicles. But over the last few months I’ve noticed a tug deep within me to explore new horizons, and I’m going to be spending dedicated time in three areas:

  1. Decarbonizing the built environment and commercial real estate. The tectonic plates in the commercial real estate market are shifting: high interest rates, downward trends in occupancy related to remote work, affordable climate technologies, the evolution of urban centers across the country. It’s a unique moment to explore the relationship between the built environment, placemaking, and climate tech.
  2. Buying and selling climate-focused main street businesses: I’ve been fascinated by the cash-flowing “boring businesses” on the front lines of the climate transition. From electricians to HVAC to light manufacturing, there are thousands of small businesses that are doing the heavy lifting of the energy transition. I’m curious about entrepreneurship-through-acquisition and the possibility of a climate-focused micro-PE fund aimed at main street businesses.
  3. Battery recycling: As we electrify everything, we’re technologizing everything, and as we technologize everything, we’re increasingly powering everything with batteries. But where will all the batteries go once their performance slips? I’m curious to explore opportunities up and down the battery value chain.

If you have ideas, projects, or connections in any of these areas, I’d love to hear from you.

On the leadership game

So much of the literature on leadership focuses on individual behaviors, individual skills, individual achievement, and individual exceptionalism, but I’m starting to think that the best leaders are often skilled game designers who create predictable relationships between cause and effect throughout their organizations. Whether leaders know it or not, their performance and behaviors establish a game that everyone begins to learn: a set of rules, incentives, and relationships between action and consequence that defines the physics of how an organization operates. For example, if a leader consistently holds people accountable to their commitments, that cause-and-effect dynamic is encoded into the game as a predictable rule. People respond accordingly.

Effective companies are the product of 1) well-designed games with 2) predictable rules that 3) create positive incentives that 4) translate into healthy behaviors. I’m learning that leaders should focus more on designing predictable, healthy, organization-wide games than on being superhuman individuals inside of them. It’s far more valuable for a leader to be imperfect in a collective, predictable game than it is for them to seek perfection in an arbitrary, unpredictable one.

On the courageous middle

As I have reflected on the wild years of 2019 to 2022, one of my biggest regrets as a CEO was to buy into a culture of performative virtue-signaling. At the heart of virtue-signaling is the idea that everything, down to our smallest action, is a statement rooted in politics and power. This concept—everything is political—sits at the heart of Ibram X. Kendi’s best-selling 2019 book, How to be an Antiracist. Kendi says either you are advancing racial equity or you are advancing racial inequity. Quite simply, he articulates in eloquent prose, there is no middle ground.

As the CEO of Uncharted, an organization that pursued social impact and social justice, I bought into these new rules. If we weren’t doing something about COVID, then we were not standing with frontline workers and those most affected. If we weren’t doing something about systemic racism after George Floyd’s murder, then our silence was a form of violence. We rushed to make statements, adopt new vocabulary, and perform our party-line politics internally and externally. It was exhausting, but also invigorating: we were playing this new game where we could score points at any time. More importantly, the consequences of non-performance loomed large: in a world thinly sliced by moral and political dichotomies, you had to pick a side. At the time, I convinced myself that this virtue-signaling was necessary—and a form of impact unto itself. Over time, however, our performative work began to compete with the organization's actual work for our primary attention.

In the years since, I’ve told myself a story that I could have chosen not to kowtow to the false equivalencies of silence equaling violence or everything being political or that our performative work was somehow as important as our actual work. I’ve felt some shame about it: why was I vulnerable to this way of thinking? Why couldn’t I have carved out a courageous middle ground and stood there?

I’ve paid close attention to the cultural moments when those courageous middle spaces get collapsed into a razor’s edge and we are forced to pick sides—when the humanity and history of complex issues and stories gets swallowed by the hunger for simple explanations.

We are again at such a moment with the conflict between Israel and Hamas: the rush to choose sides, the attempts to vindicate oneself publicly, the collapse of nuance. People are being harangued for what they have said and what they haven’t said because we’ve been tempted by the idea that there is no middle ground.

Part of this is a consequence of cultural ideas, and part of it is a consequence of participating in arenas where everyone believes they’re being watched. Digital media platforms that enable everyone to speak are such panopticons: we thought platforms of distributed voice would become 21st-century digital town squares for diverse expression and connection. Instead, they’ve become the primary arenas where we convey our self-vindication and parade our rectitude. All of this makes me ask a bigger question… a question I wish I would have asked myself as the CEO of Uncharted: what games have I unwittingly entered whose expectations and rules I am now following? Maybe even that question is somehow political, or maybe it’s just an invitation to make the radical choice of tuning everything out and slowing down enough to determine what ground I actually stand on.


What I am reading

  • The lost art of recovery. How the fast pace of modern society has made us forget the need for convalescence. The New Yorker.  
  • How AI is being used to spread disinformation during a war. In the Israel-Hamas conflict, its use and impact has been quite unexpected. WIRED.
  • The trend of returning to the office for a 5-day workweek is dead. Why hybrid work is the new normal. The New York Times.
  • The techno-optimist manifesto by VC Marc Andreesen is an important read for those seeking to understand technology and society (even though I found it to be rather vacuous and scattered). Substack.
  • AI image generators are reducing the world to stereotypes of different cultures, countries, and people. Rest of the World.
  • Carbon offsetting is critical for us to hit net-zero goals, but it’s full of scam-artists and questionable math. The New Yorker.
  • The sea change in our economy, and what it means for investors. A lucid and compelling memo by Howard Marks. Oak Tree Capital
  • We have long thought of climate change as a technological and economic problem. But it is also a democratic one. Can our political institutions quickly facilitate 91,000 miles of transmission lines? The Atlantic

Something personal

I ran my first half-marathon a few weeks ago. It wasn't a particularly impressive performance: I didn’t run that fast or post an impressive time, but as I crossed the finish line I found myself overcome with emotion, my eyes welling with tears. This half-marathon was the first individual athletic competition I’ve entered since high school, and I was struck by how different it was than a simple jog in the park. I think it’s actually quite rare when the low, muted drumbeat that sets the tempo for most of our lives quickens, when a moment becomes elevated, when we find ourselves somehow—rather unexpectedly—really trying to do something daunting, where our own individual performance might tell us something we’re surprised to learn about ourselves. Maybe such moments are more available to us than we think. Maybe, if we’re willing, even an ordinary Sunday morning can make us feel so alive it brings us to tears.