25 Tantilizing Truths about Doing Business in the 21st Century (So Far)
The biggest challenge you face is understanding your current position and the assumptions you're making. Orientation is everything.
Latest
How to design your own demise + midyear book recs
Even if you don't care about Elon, Tesla, or X, Ms. Yaccarino's exit from X is a Rorschach test for all of our leadership. Anyone who is trying to build in this post-trust system will find something of themselves in this story, and some of it might not feel so good.
First Date Marriage Proposals
Most firms are so accustomed to getting married out of the gate that they're still shocked when customers aren't interested in the proposal. You have to fundamentally alter the sales process if you want to make it to the altar.
How to Escape a Venomous Web
Everything you're spending time, energy, attention, or money on on the Internet should be driven by specific boundaries. It's to stop being Silicon Valley's lunch.
Stop Educating Your Prospects
The initial dream of the internet was a sharing of information. Too bad that's over. This essay is about eating my own cooking, serving it to you, and doing what's necessary now.
We make zombies here.
We’ve built a system that rewards surface-level performance and punishes depth, propping up dead companies with borrowed time and fake metrics. If you want to make something alive, you have to risk being real.
Less Marketing, Less Tech
Marketing as we know it is collapsing—platforms like Google and Meta have outgrown their need for us, their bots ending the game of traffic. We must shift our focus, resist algorithm-driven inauthenticity by showing up as our real, human selves.
The New Leadership School
Edition 122: The requirements for turning leaders into more leaders
Not much keeps me up at night. Other than chronic pain, that is. Living with chronic illness is a really fun time, but that's a newsletter for a different day. One of the side benefits of living with
How Founders Beat Uncertainty
Right now, a lot of businesses are operating from a place of contraction. Taking what they can from a shrinking pie. But the winners? The ones who will make it through this moment and thrive? They’re not focused on getting a bigger slice—they’re focused on making a bigger pie
The only two things I require of a leader
All growth is change, and that starts with the leader, but it's gonna require more of you than ever before. Before we start a growth project, I test leaders on two things, and literally nothing else really matters after that.
It's not you. It's the *gestures broadly* this 👉
This polarization and degradation of trust at scale is incontrovertible and organizations that ignore its effects on how buyers buy and clients trust do so at their peril. Leaders say, "We don't know what happened. We used to have no problem getting new clients, now... if we're honest..."
You have to choose
Leaders imagine deep impact while running a business on "wide" actions. Margins are consumed. Prospects are confused.
You can't be both broad and deep without spending ungodly amounts of usually someone else's money. It's time to decide.
Gratitude is magic
2025 Week 5: Headlines, Hubris, and Happy Places
💡Upcoming Opportunity: If there is one place where firms need to check their ties to the status quo its in content strategy. I'm laying out my rules for content and answering all your related questions in our second online forum
What's the best advice you gave this week?
Most founders/CEOs convince themselves that if not for them, the entire growth enterprise would collapse into itself, but the truth is, the executive suite is the primary reason why content operations fail and why brands underperform. Good news is, they can fix it.