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San Juan Islands, Washington  ·  August 20–24, 2026

D8 Leadership
Summit

Strategic Fishing Operations
“A board offsite. With salmon. And consequences.”
SYC Outstation Friday Harbor Henry Island Roche Harbor
The Brief

At a Glance

Five days. Two boats. One real conversation a day — and a trophy on the line.
Competition

The D8 Cup

A two-boat fishing contest — Serenity vs. Gilly — run down the western shore of San Juan Island. Scored, calcutta'd, and settled at dinner.
The Real Agenda

Leadership Track

One sharp question set aside each day for the leadership team and advisors — vision, strategy, people, and what year two demands of us.
Basecamp

Henry Island

The SYC outstation near Roche Harbor is home for three nights. Serenity holds the dock; firepits, whiskey and cigars, and poker hold the evenings.
Mission Brief

Day by Day

Operations up top, the agenda item that matters down below.
Thu
20
Aug

Muster & Departure

MorningAll hands aboard Serenity at the Hotel Bellwether dock, Bellingham — by noon, no exceptions.
AfternoonCast off for Friday Harbor. Overnight at the SYC Friday Harbor outstation.
EveningDinner in town, then the opening “board meeting.” Shawn & Simon arrive tonight aboard Gilly.
Agenda Item · Day One
Destination
“If we're wildly successful three years out, what's true that isn't true today?” — everyone answers solo first, then we compare.
Fri
21
Aug

The Western Shore Run — & The D8 Cup

MorningBreakfast aboard, then both boats run the west side of San Juan Island toward Henry Island.
On WaterSalmon on the troll, orca watch in Haro Strait, and the inaugural D8 Cup — Serenity vs. Gilly.
EveningBase up at the Henry Island outstation. Fresh-catch dinner at camp. Firepit, whiskey and cigars, poker.
Agenda Item · Day Two
Vision & Strategic Intent
“What game are we playing, and what's our unfair way of winning it?” — wedge vs. platform, said in one sentence the whole team can repeat.
Sat
22
Aug

Henry Island Operations

DayFishing, shrimp pots, and island exploring out of basecamp.
EveningDinner at McMillin's in Roche Harbor — prime rib and Northwest fine dining on the water. Back to camp for firepit, whiskey and cigars, poker.
Agenda Item · Day Three
Strategy → Execution
The two or three bets for the next twelve months — and what we explicitly won't do. Plus the move from 20 to 50: decision rights, ownership, where we're still single-threaded.
Sun
23
Aug

Catch, Cove & Camp

DayMore fishing, shrimp pots, and exploring. Oyster lunch at Westcott Bay (tender in — small dock).
EveningDinner at the outstation, on the day's catch. Firepit, whiskey and cigars, poker — and the dark-sky night.
Agenda Item · Day Four
People, Culture & Leadership
The behaviors we won't let dilute as we hire, an honest key-person read, and how each leader's own job has to change now that they can't be in every room.
Mon
24
Aug

Cruise Home

MorningBreakfast aboard, then the cruise back to Bellingham.
ArrivalDock at the Hotel Bellwether, early afternoon.
Agenda Item · Day Five
Commitments & Cadence
Each leader names the one or two things they own coming out of this. We write down the decisions we actually made — and set the rhythm so they don't evaporate.
Competition

The D8 Cup

Serenity vs. Gilly. Friday's run decides it.
King Chinook5
Silver Coho3
Pink Humpy1
  • Only legal-retention fish score — or photo on the measuring board if you'd rather release.
  • Biggest fish of the weekend runs the Calcutta — the Thursday-night auction where you buy shares in the field. See the addendum.
The Stakes
  • Losing boat buys the first round at McMillin's on Saturday.
  • Winning skipper holds the Cup until next year.
  • Bragging rights compound annually.
Honors

Awards & Recognition

Engraved, presented straight-faced, named like a proxy statement.
Chairman's Award for Operational Excellence
The quietly competent angler — the one who just produces.
Most Promising Pipeline
Biggest talk, emptiest creel. Forward-looking statements only.
Material Adverse Event
The weekend's finest mishap. Disclosed in full.
Going Concern
Outlasted the whiskey and still made breakfast.
Challenge Coins

A custom D8 Summit coin for every attendee — the keepsake that outlasts the trip.
Coin Check

At the firepit, any man may call a coin check. No coin on you — you buy the round. Carry it.
Off-Hours Operations

Traditions & Standing Bits

Played straight. Kept short. That's why they work.
Thursday Night

The Opening Board Meeting

One-page agenda, a gavel, mock minutes, and absurd officer appointments: Treasurer holds the calcutta, Sergeant-at-Arms runs the firepit, Investor Relations owns the recap. Ten minutes, hard stop.
Firepit

Whiskey Due Diligence

Everyone brings a bottle. One night, a blind flight — ranked, scored, and a house pour crowned. Cigars pair naturally. Findings are non-binding.
The Artifact

The Shareholder Letter

A drone over the two-boat run — orca and a race make genuinely great footage. A produced recap reel and a deadpan one-page “annual report” land a week after we're home.
Opt-In

Cold Plunge & Dark-Sky Night

A bracing plunge off the boat in a quiet cove — coin or bar credit for the brave. And one night at Henry Island we kill the lights and let the sky do the work.
The Real Agenda

The Leadership Track

Year one is behind us. The question underneath all of it: are we still a project, or are we becoming a company?
  • Thursday — Destination. Where we're actually trying to go, surfaced before we argue tactics.
  • Friday — Vision & Strategic Intent. The one game we're playing and our unfair edge, in a single sentence.
  • Saturday — Strategy to Execution. The year's two or three bets, what we won't do, and building for 20→50.
  • Sunday — People, Culture & Leadership. What we protect, where we're exposed, and how each of us leads differently now.
  • Monday — Commitments & Cadence. Owners, decisions on paper, and the rhythm that keeps it alive.

House rules: one sharp question per session, about an hour, hard stop. One person facilitates, one quietly captures — and that capture becomes the shareholder letter. Customers and investors stay in the room as a reality-check lens, not a separate meeting.

Pre-Work · The Only Homework

Arrive with one written answer to Friday's question: what game are we playing, and what's our unfair way of winning it? A sentence or two. That's it.

Order of Battle

Vessels & Standing Orders

The Fleet
Serenity
Mothership and basecamp. Carries the group, holds the dock at the Henry Island outstation.
Gilly
Shawn Gilfedder & Simon. Primary fishing operations and the other half of the D8 Cup.
The Tender
11′, five aboard. Shuttle duty, shore runs, and the Westcott oyster landing.
Standing Orders — Pack This
  • WA fishing license + salmon catch record card. Mandatory — no license, no line in the water.
  • Layers and a proper rain shell.
  • Non-marking deck shoes.
  • Sunglasses, sunscreen, motion meds if you need them.
  • Cash for the calcutta and the poker table.
  • A bottle for the communal whiskey stock.
  • Your one written answer to Friday's question.
Still To Confirm
  • Friday Harbor dinner spot (Thursday night).
  • Final headcount — drives tender runs & the McMillin's reservation.
Book Early
  • McMillin's, Roche Harbor — Saturday dinner (peak August; reserve on Resy).
  • Westcott Bay — Sunday oyster lunch.
Addendum

How the Calcutta Works

Thursday night, every angler goes public. You're not betting on yourself — you're buying equity in each other.
The IPO · Thursday Night

The Auction

The Treasurer puts each angler up one at a time. High bidder owns that angler's shares for the weekend. Like your own odds? Buy back a piece of yourself at the going price. Every winning bid is pooled — that pool is the pot.
The Settlement

The Payout

Scored on the single biggest fish of the weekend — Friday through Sunday, all in play. When it settles, the owners of the top finishers split the pot — and the man who actually lands the winning fish keeps a founder's cut, no matter who owns him.
House Rules
  • The D8 Cup (boat vs. boat, Friday) and the Calcutta (biggest fish, all weekend) are separate contests — win one, both, or neither.
  • Biggest fish is settled by length on the bump board, photographed, with one witness from the other boat. A released fish counts off the photo.
The Conceit
  • Thursday's auction is the IPO. Buyers are shareholders; the catcher holds founder's equity.
  • The Treasurer holds the book and files results in the annual report. Settled at the final firepit.
D8 Leadership Summit
San Juan Islands · August 20–24, 2026
Dates locked. Agenda final draft. Bring your line in the water and your one good question.