Sailing Against the Current of Frictionless AI

He encourages questioning what you read and taking the other side, even if you (or anyone you are around) doesn’t believe it. This isn’t to be contrarian for the sake of it but instead to push yourself into a friction-filled point of view outside of the bubble you may be in.

leaves room for spontaneity and problem-solving by introducing strategic uncertainty , planning projects or acting on ideas without detailed itineraries: “Committing to things beyond your comfort zone is the only way to build adaptability and resilience.”

He incorporates physically demanding work into regular life to get out of the headspace and “above the shoulders” world of software and the internet, and engage other practical senses and skills (gardening, woodworking, repairs) that ground you in the present.

He tries to focus or limit sources of “frictionless consumption ,” though he’s not an absolutist: “That kind of stuff has a time and place, particularly if you’re stuck on a problem. Sometimes, procrastinating on something simple or distracting can allow the right thought to appear.

conducting research, he prioritizes curiosity over canonical paths , often taking unconventional routes through the work. Though this approach can lead to roundabout explorations, he believes starting where genuine interest lies ultimately reveals the most critical insights

To avoid impulsively “just shipping it,” he introduces deliberate friction through cooldown periods when reviewing designs or providing feedback. This intentional pause allows ideas to mature, fostering more thoughtful and meaningful responses.

He often turns to analog methods of early creation , like sketching on paper or handwriting notes, instead of immediately resorting to digital tools. The slower pace offers deeper focus and naturally restricts the ideas to their simplest.

When working with portfolio companies, he opts for hands-on involvement . This approach establishes trust and partnership with founders, providing firsthand insights essential for offering feedback.

He avoids auto-scheduling tools , believing that manually coordinating meetings preserves his intentionality and responsibility over his time.