The Insider - June 2022

On crypto frontiers, servant leadership, regenerative work, and father-son trips.

The Insider - June 2022
Photo by About Maps / Unsplash

Hi everyone,

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

On Frontiers

After years of navigating a social sector averse to risk-taking, I found myself intrigued by a space experimenting and building at a new frontier: web3. I am no web3 expert, but I love exploring frontiers, and the driving question guiding my curiosity was: “How can web3 create a more just and equitable world?”

I wrote a White Paper earlier this year researching the intersection of web3 and impact as a way for me to try to answer this question (next white paper coming soon), and I continued this exploration by teaming with Kila Englebrook and Kyle Westaway to organize an in-person event in Austin, Texas earlier this month: The Web3 Impact Summit. We convened a range of speakers who were shifting the power dynamics in philanthropy through DAOs, bringing carbon credits onto the blockchain, and infusing principles of equity and inclusion into the metaverse. Five hundred people applied to attend our 100-person event, and we were humbled by the momentum and curiosity of people asking similar questions.

Nothing animates the enthusiasts and skeptics quite like something still in its infancy. This is to be expected at any frontier: the thing that’s emerging hasn’t yet fully come into view. We’re pressured to take sides too early, which leads to sweeping opinions propelled forward by our confirmation biases. At such a frontier, I believe the appropriate response is a commitment to reasoning by first principles and the intellectual humility to acknowledge how much we still don’t know. For more on the intersection of web3 and impact, Kyle Westaway and I are highlighting articles and journalism in a monthly newsletter.

On Regenerative Work

We’ve designed our working lives the way we’ve designed our industrial farms. We mono-work the way we mono-crop. But the indigenous wisdom of regenerative agriculture might have powerful applications in the workplace. Soil health, rotational grazing, and fallow fields are all metaphors for restoring health to the workplace and to ourselves. What might it look like to consider regenerative principles in how we structure our workweeks, our time-off, our sabbaticals? When we flatten the natural cycles, when we ignore the seasons, when we forget that compartmentalizing our lives and our fields is an illusion, then we can expect the same outcomes in the workplace as we expect in industrial farming: eroded soils and souls. What will it take to create organizational cultures of regenerative work?

On Servant Leadership

I grew up with the idea that the best leaders were the servant leaders. They were sacrificial for their team, giving fully of themselves and leaving it all on the field. There was a time as the CEO of Uncharted when I took the idea of servant leadership too far, telling myself a story that good leadership was about shielding the rest of the team from the bad stuff. I convinced myself that I should behave like a plant performing photosynthesis that turned toxic carbon dioxide into clean, rich oxygen. Servant leadership, I believed at the time, was a function of breathing in the external problems of the business and then magically breathing out serene equanimity and abundant optimism to our team (sometimes I take my biomimicry metaphors too far).

But as my sabbatical has set in, I’ve been working with my therapist to examine the narratives underpinning my relationship to leadership, and I am reminded that I am no plant; I possess no superhuman powers to turn carbon dioxide into oxygen, and the times when I told myself I should be a photosynthetic leader were exactly the times when I felt most alone, most burdened, most tired. What starts with an obsession to protect others often ends with a realization that we haven’t been protecting ourselves. What starts with a belief that we can be superhuman often ends with the realization that we are nothing more than human. There is a gentleness when we negotiate the space between our audacity and our acquiescence.

What I am reading

  • How San Francisco became a failed city, the myopia of the progressive agenda, and what to do about it. Here.
  • What does the crypto crash mean for the future of blockchain based technology? How we need historical perspectives to understand current events. Here.
  • The resilience of rural America displayed through the buildings and architecture of tiny towns. A photo essay.
  • Podcasts: America After Roe: A Roundtable and The Yale Law Professor who is Anti-Roe, but Pro-Choice.
  • Book: Four Thousand Weeks by Oliver Burkeman. One of the best books I’ve read in the last year on the finitude of time, the pointlessness with our obsession with productivity, and how to embrace the long defeat.

Can you help?

  • Future of Work Newsletter: I’m starting a new, separate newsletter for business leaders on the future of work. From the 4-Day Workweek to building a world-class culture to staying on the cutting edge of the latest trends in the workplace, the Smart Workweek Newsletter will cover it all. Sign up here.
  • Who is the best illustrator you've ever worked with? I'm working on a creative project and looking for an illustrator (or a few!).

Something personal

Every few years, my brother and I take a father-son trip with my dad, and this year we traveled to San Diego to visit an aircraft carrier and diesel submarine anchored in the city’s harbor. My grandfather (my dad’s dad) was an admiral in the Navy, the commander of a submarine, and the hero in the rescue of his crew after his submarine partially exploded and ultimately sank in the arctic seas during WWII. In San Diego, we ducked through the cramped, claustrophobic quarters of this WWII submarine. We asked questions about our dad growing up, about our grandfather, about submarine warfare and PTSD and being depth-charged 500 feet below the waves…we asked questions we never asked before and we heard stories we never heard before. No matter how familiar and intimate we are with the people and places in our lives, there is always another story, waiting to be surfaced, ready to come up for air.


Standing with women and believing in the power of their choices,