Starting a book club in Toronto. Inspiration from @thesamparr Anti-MBA club. Bi-weekly meet-ups at Ace Hotel. Who's in?

the single greatest thing you can do for your sanity is to take life seriously. we live in a profoundly irony-poisoned society and you cut off 1/100th of what life can offer you by being a goofball. the jester may be near the king but he does not sit at the hand of the father

2025: the year of OpenAI and Quest diagnostic wrappers

Inline interview w/ the “meandering” @ChrisJBakke Who doesn’t love a good “see response inline below” Other than when it’s from a lawyer or boss

Congrats to the entire Beacon team on the Series B! If you are interested in GM opportunities at Beacon Software, don't hesitate to reach out.

My good friend @GinsburgRandy, just made the move from NYC to SD. If you're in SD and looking to hang with a 10/10 human, shoot him a dm

The topic of organization design in an AI world seems to be a recurring theme not only with startup peers but also with CEOs of mature scaled businesses. In a quest for feedback/pushback and also to try to be helpful I wanted to share how I am thinking about org design in the age of AI: Design Principles: a) Speed of decision making and execution: As AI reduces barriers to competitive entry and increases customer expectations, survival will require ‘big’ decisions to be made quickly, and changes to be shipped immediately. In a world where agents can coordinate tasks amongst themselves instantly and 24/7, the market will expect an instant problem → response loop. Organizations need to be designed to allow for that to happen. b) Minimize layers: So much of traditional org design has been about balancing between spans-of-control, and the number of layers between executives and the lowest org levels. Spans become irrelevant in a world where executive bandwidth grows exponentially. Middle layers that exist to gate, summarize or cascade information will be irrelevant as every environmental input is converted into a piece of data, which is subsequently synthesized and acted on by PhD level AI agents. Implications: 1) End of the ‘Coach’ Only Role: Every leader will have to be a player first and coach second. When the content and nature of work are changing so quickly, the only way to be an effective coach of others is to know the work yourself. 2) The Death of Functions: In an environment where any question, regardless of how complex, is answerable with a $10/month subscription humans will no longer be defined by technical specialization. When knowledge is commoditized, roles built solely on specialization become irrelevant. 3) Impermanence: I am convinced no one really knows what the next five years will look like as AI invades our lives. As a result, org structures will be built and destroyed quarter-over-quarter if not month-over-month. 4) CEO of Control Center: The modern CEO will be less of a strategist or cheerleader, and more of an F1 driver. They will spend their days interpreting real-time telemetry, responding instantly, and orchestrating both humans and machines. It is a shift from planning to navigating. If you are building or retooling your organization in this environment: A) Treat your structure as temporary B) Redesign roles around outcomes not functions C) Hire leaders who do work, not just manage or inspire D) Decide if you want to be in the cockpit of your race car I shared these thoughts on “Org Design In An AI World” in a recent blog post. The link is shared below

Love this line by @GrahamDuncanNYC, on hiring: "One of the greatest gifts we have for each other, for our children and spouses, for our teammates, is the positive feedback loop we can put someone into purely by believing in them, by seeing their genius and their dysfunction clearly and then helping them construct conditions for the former to flourish."

I was listening to @tyger_cho’s podcast with @EricJorgenson (big fan of his work) During the podcast, Erik brought up the notion of ‘lost years’ “The more peoples stories you study the more you see there is always a period of time unless you dig, it’s not obvious that the person was working on their craft, but if you know the story well anything that looks like an overnight success was not.” I loved hearing his story of working at a startup for almost 10 years before writing The Almanack of Naval. He talked about starting a project called Evergreen and how instrumental it was to honing his craft as a writer and meeting people that played an instrumental role in his books success. It made me reflect on my own projects like Deal Bridge, 535 or my monthly newsletters Each one has been a meaningful step in sharpening my craft

I’ve recently gotten access to a very ‘well-respected’ research publication. After trying to pitch an investor friend on one of the investment theses, I received some valuable feedback from him. He’s an incredibly smart investor. The below speaks to the value of skepticism and the importance of understanding incentives:

“The actions of those that have achieved great things are often illegible to most outsiders in the present. It’s only looking back that those around them can make sense of their choices in life"