FIELD & FATHOM | No. 028
Daily Letter · Mindset Operating System · 8:42 PM
TRIVIA | Category: Sport & Business
Start here. Answer at the bottom.
Before becoming one of the most respected venture capitalists in Silicon Valley history, an early backer of companies that changed how the world shops, eats, travels, and communicates, he was a Division I college basketball player standing six feet nine inches tall. He has written one of the most widely read investor newsletters on the internet for over two decades. His latest book is about building a career you will not regret. Who is he?
THE ORIGIN
Seaforth Marina sits just off the water in San Diego, the kind of place that does not announce itself and does not need to.
In 2011 I crossed that stretch regularly on a beach cruiser. Sometimes it was a smooth ride over from Ocean Beach where two of my closest friends were living at the time, the kind of ride where the city falls away before you even realize it has. Sometimes it was a thirty-minute pedal from further out. The kind of distance that requires a decision. A commitment. A reason to go.
I always went. By bike, by board, by car when I had to. Never announced. Never planned too far in advance. Just there.
The cracks in the asphalt on the approach were spaced almost perfectly. Every few rotations of the wheel gave you just enough feedback to stay present, to feel the difference between moving through something and actually being in it. The bridge. The turn. The chain running parallel to the dock path under my right hand as I slowed down and let the marina come into focus.
The halyard clanging against an aluminum mast. The low groan of dock lines pulling taut against cleats as the tide shifted. Fenders squeaking against the hull. A bilge pump cycling on somewhere in the middle distance. The hollow knock of fiberglass nudging wood. Rigging singing in a light wind off the bay. And somewhere above all of it, seagulls settling an argument over whatever crumbs had been left near the slips.
Early mornings there moved at their own pace. Each boat in its own slip. Its own lane within the harbor. Each one carrying a story that would take years to fully understand and probably longer to earn the right to hear. The people moving around those docks had been somewhere the sea does not negotiate with you. They had come back. They had found their lane and docked in it, now rising and falling with the tides that rolled into port. Not in defeat. In the particular peace of someone who has navigated open water and knows the difference between chaos and the harbor waiting on the other side of it.
I sat on that bike, one hand on the handlebars, one hand resting on the marina chain running parallel to the dock, and let it do what it always did.
I knew I would one day build something called Harbor Lane.
Not a plan. Not a pitch. A knowing. The kind that arrives in quiet places when the mind finally runs out of things to chase and something older and steadier takes its place.
Harbor Lane Holdings. Harbor Lane Company. Harbor Lane Capital.
Each boat finds its lane within the harbor after navigating the open water. Each one docks alongside vessels that have their own stories, common ground shared between people and crafts that have all been somewhere difficult and found their way home.
That is the company. That is the name. That is Seaforth Marina in 2011. A smooth ride over from Ocean Beach or a thirty-minute commitment from further out, either way, always worth the trip.
An origin story I am proud of telling.
FIELD REPORT | Read Your Opponent
Every opponent gives you information every two to four seconds.
Most players never collect it.
Reading your opponent on the lacrosse field is one of the most trainable and most undercoached skills in the game. It is the difference between a player who reacts and a player who anticipates. Between a player who is always a half-step late and one who always seems to have more time than everyone else on the field.
Here is what to look for and how to use it.
The weight. Where is your opponent's weight loaded right now? A defender on their heels is a step slow, attack hard, change direction decisively, the first move wins. A defender balanced and on the balls of their feet is ready, be patient, use a fake, make them commit before you do. You can read this from a stick-length away. Most players never look.
The hips. Hips tell you direction before the feet do. A defender whose hips are turned even slightly toward the crease has opened a lane to the outside. A midfielder whose hips are square has taken away the dodge but left the pass available. Read the hips and you are reading the play a full beat ahead of everyone else.
The stick. Where is the defender's stick positioned? High means the low lane is available. Shaded to your strong hand means the weak-hand dodge is there. A passive stick means they are waiting for you to commit first, give them a move that is not your move, watch whether they bite, then go where you actually intended.
The eyes. Elite defenders watch your hips. Elite offensive players know this and use it. A quick look off, a glance to a teammate, a subtle head fake, tells you instantly whether your defender is locked onto you or helping elsewhere. That half-step of information is everything at this level.
Going punch for punch. The best individual matchups in lacrosse — the ones that decide games, are won by the player who keeps adjusting. Round one you make your move. Round two your opponent takes it away. Round three you adjust again. The player who makes the most adjustments within a single game, who reads, reacts, and recalibrates faster than the person across from them, wins the matchup regardless of who has more physical gifts.
Your opponent is giving you clues every two to four seconds. The question is whether you are paying attention.
MINDSET OS | Tame the Monkey Mind
There is a term from Buddhist philosophy that Mark Divine builds his entire Unbeatable Mind framework around, the monkey mind. The untamed mind that swings from branch to branch, thought to thought, never settled, never fully in the moment it is actually standing in.
Divine spent twenty years as a Navy SEAL and another decade teaching the principles of mental toughness to thousands of people. The foundation of everything he teaches begins in the same place, gain control of the mind before the mind controls you. Not through force. Through breath. Through front sight focus. The deliberate act of returning attention to the present moment by coming back to the breath, again and again, until the practice becomes the default.
The monkey mind cannot survive in a marina at six in the morning. Something about the pace of that place, the tide doing what the tide does, the boats moving without urgency, the sounds arriving and settling without needing your response, does the work that breathwork is supposed to do. It returns you to yourself before you even try.
That is the practice this week. Find your Seaforth Marina. It does not have to be water. It is the specific environment, the walk, the early hour, the thirty-minute bike ride that requires a decision, that returns you to yourself when everything else is loud. Go there deliberately. And in that quiet, before the noise returns, ask yourself one question:
What am I building, and why does it still matter to me today?
Write the answer down. That is your front sight. That is your harbor.
TRIVIA ANSWER | Category: Sport & Business
Bill Gurley. Division I basketball player at the University of Florida. He went on to become a general partner at Benchmark, one of the most successful venture capital firms in Silicon Valley history, with early investments in Uber, OpenTable, Stitch Fix, Nextdoor, and Zillow. His newsletter Above the Crowd has been required reading in the technology and investment community for over two decades. His latest book, Runnin' Down a Dream, is about building a career you will not regret.
ON ROTATION | What's Playing
Some music finds its audience the slow way, and holds up longer because of it.
Daily Rotation: Over and Over Again (Lost and Found) — Clap Your Hands Say Yeah, Clap Your Hands Say Yeah (2005)
A Philadelphia band that self-released their debut album in 2005 with no label, no marketing infrastructure, and no plan beyond the music itself, the album spread entirely through early MP3 blogs and word of mouth until David Bowie acknowledged he was a fan, a major-label bidding war followed, and the band famously turned every offer down. Over and Over Again (Lost and Found) is the song that feels most like a marina in the early morning, a pleasingly uptight, twitchy urgency underneath a melody that somehow stays calm, like a boat rising and falling in a slip while the city moves at full speed on the other side of the gate. NPR's All Songs Considered named the album one of the fifty most important recordings of the decade. Put it on tonight and then let the full album run — thirty-eight minutes of one of the great DIY stories in modern music, built exactly the way Harbor Lane is being built, on its own terms, in its own time.
ABOUT THE AUTHOR
Kyle Smedley is the founder of Harbor Lane Holdings, building at the intersection of sport, people, and capital.
Career stops include Events.com, Lombardi Contracting Corporation, and DPR Construction. Today he leads Atticus Lacrosse Company, working alongside Mad Dog Lacrosse and Ravenscroft School, and Harbor Lane Company, operating across real estate, private equity, and talent placement.
Field & Fathom goes out every night at 8:42 PM.
Reach out directly: [email protected]
Until tomorrow,
Kyle Founder · Harbor Lane Holdings · Atticus Lacrosse Company
Field & Fathom · Harbor Lane Holdings · Daily
Powered By People Who Keep Showing Up

Proud Sponsor
Stop Fine-Tuning Models You Don’t Need
Fine-tuning sounds like the answer until you factor in the cost, the data pipeline, and the six months before a bigger model makes yours obsolete. Most of the time, prompt engineering or better context gets you there. But sometimes it doesn't — and that's where things get interesting.
In this free night session, Aaron Gallant covers the real tradeoffs behind fine-tuning LLMs, from synthesizing training data with frontier models to running PEFT and QLoRA on constrained hardware. You'll learn when smaller, specialized models actually beat throwing money at a bigger one — and why data curation is the work nobody wants to talk about. Built for engineers who want to make the right call, not just the cool one.
Live and remote. Wednesday, June 3 at 5 PM CT. Register now.

