Hi everyone,

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

Thank you

In response to my eulogy of Emma in the last Insider, many of you reached out to share your own stories of losing a pet. They were beautiful and heartfelt. Thank you for taking the time to respond. I read every one.

On leadership

I used to think that great leaders took action—that the leading was in the doing. But then my perspective began to change. The more a leader tried to actively manage their team, the more likely it was that they were the ones being managed. 

Meanwhile, the best leaders I watched were taking a more indirect approach. They regarded themselves as game designers, designing the set of expectations, incentives, and accountabilities—rules of the game—that shaped the behaviors of their team. They spent time creating the motivations for succeeding, the consequences for failing, and a set of rules that articulated what is tolerated and what is not. Here are four principles of leadership through game design:

  1. Actions have consequences. As a manager, your team will notice what you tolerate far more than they will remember what you say. The edges of our tolerance—what we tolerate and what we don’t—shape our team’s ability to self-correct and stay focused.
  2. Leaders pay attention. For leaders of fast-moving organizations, it’s easy for commitments to get lost and follow-through to get dropped. By creating a system that allows you to maintain visibility and hold your team accountable for the work over time, your team will do a better job at managing themselves. You can do far less active managing when your team knows that nothing gets by you.
  3. Every expansion requires a corresponding contraction. Effective delegation treads a fine line: get too far out of the way and performance could slip. But stay too involved and people could feel micromanaged. The mistake I’ve seen myself and other leaders make has been to delegate without its equal and opposite counterforce. Delegation is an expansion, and it needs a commensurate restriction elsewhere. Delegation without focus leads to too many competing priorities. Delegation without standards of excellence leads to poor quality. Delegation without reinforcing values and behaviors leads to inconsistencies in culture and performance.
  4. Be the leader you wish to see in your organization. Whether you realize it or not, your personal behavior, style, and performance are the biggest predictors of how your team will show up at work. It starts with a question: What behaviors am I modeling, and how do those behaviors reinforce or undermine the behaviors I want to see throughout the organization?

On relatability

Presented to me as one of the more peculiar conversations I would listen to this year, I sat down two Saturdays ago, poured myself a cup of coffee, and took in a conversation between David Marchese, a New York Times journalist, and his guest, Andrew Schultz, a comedian-turned-podcaster. I couldn’t look away. It was a disaster.

The conversation—which explored the differences between the institutional approach to professional, erudite journalism and the freewheeling, personality-driven style of today’s podcast bros—was itself a manifestation of that very topic. Marchese, hemmed in by his own inhibitions around journalistic ethics and standards, delivered an embarrassing performance: inauthentic, unsettled, robotic. Schultz, by contrast, was at ease—conversational, self-reflective, human.

It was a microcosm of bigger trends: the hollowing out of mainstream media, the rise of podcasts anchored by relatable personalities, and the consumption of news through people we actually trust, rather than institutions we’re supposed to trust.

Later that day, I attended my first Savannah Bananas baseball game, a delightfully adapted baseball game whose founder built a sport centered on just one thing: obsessing about the fan experience. In the same way that Marchese told Schultz, “You’re not a journalist,” the MLB has decided that the Savannah Bananas are not baseball. And yet, Schultz and the Bananas question such labels. “This isn’t the Globetrotters. We’re building a sport,” Banana’s owner Jesse Cole said, as he sells out stadium after stadium.

Is it inevitable that an incumbent should dismiss a challenger as no competition at all? Is it another example of hubris? If there is a lesson here, perhaps it is to remain in touch with what business you’re actually in. For the challenger, a strategy that focuses on customer obsession can capitalize on the overconfidence of even the most established institutions. For the incumbent, the work is harder: to remove every self-assurance that one's position is secure and to ask oneself again and again: what business are we actually in?

On rushing vs. discerning

Zusha was a Rabbi born in the Polish town of Hanipol in the 18th century. A holy man and one of the leaders of the Hasidic movement within Judaism, he is known to have wept on his deathbed. His students tried to affirm him; he was almost as wise as Moses or as kind as Abraham. Surely, he would be judged favorably by God. 

Zusha replied, “When I pass from this world and appear before the Heavenly Tribunal, they won't ask me, ‘Zusha, why weren't you as wise as Moses or as kind as Abraham,’ rather, they will ask me, ‘Zusha, why weren't you Zusha?’”

Is the lesson obvious? Just be yourself. Go live your life. Don’t compare yourself to everyone else. But it’s actually quite hard to distinguish what we want from what we’ve been told we want. That distinction requires time and work and the willingness to be lonely—to let the sirens of comparison and conformity pass us by, and then to design a life that sets us apart from our heroes and our peers. When we stand before the Heavenly Tribunal, and they ask us, “Why weren’t you you?”, the most honest answer we might give is that we never slowed down enough to figure out who that person was and what they deeply wanted.

Should we work together?

For every $1 spent on email marketing, companies generate, by some accounts, $42. Email is (still) one of the highest ROI channels to reach your audience. Yet, it’s never been harder to stand out in the inbox. The companies that get the highest ROI don’t just sell products and promote themselves—they build long-term, human relationships with insightful editorial newsletters.

This is why my company exists. Future Forest makes it effortless to send premium newsletters that cut through the noise. We manage every step of the process so you can build trust in the inbox—at a fraction of the time. If you’re interested, we're accepting new clients for an October 1st start date.

What I am reading

  • This podcast about Alpha School stopped me in my tracks. For anyone interested in the future of education, it’s a must-listen. Colossus.  
  • The explosion of international travel has transformed historic places like Florence and Kyoto into Disneyland tourist traps. But does anyone mind? New York Magazine.
  • In the age of AI, there’s a benefit in making things difficult. Why embracing friction in a world of frictionless ease is the key to breakthroughs. Willem Van Lancker Substack. 
  • There are two major demographic trends underway globally: the aging of our population and the urbanization of our civilization. The Polymath Investor.
  • One of the most delightful reads of the month: The history of the New Yorker’s vaunted fact-checking department. The New Yorker.
  • Greenland is the new land of opportunity for those seeking to cash in on rare earth minerals. Bloomberg.
  • Can an Italian textile mill make it in America? A profile of an entrepreneur trying to bring old-world European craftsmanship to America. The New York Times.

Something personal

In last month’s Insider, I eulogized our dog Emma by writing:

“It is the dawning recognition that sometimes our dogs, who have faithfully followed at our feet, don’t get to walk with us into the next chapter that they have been quietly, knowingly preparing us for all along.”

It was foreshadowing a new chapter that Emma had been preparing us for all along. Lisa and I are expecting a baby boy any day now. He will be born at the same hospital where I was born, almost 38 years ago.

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