What We Can Learn from a Whale Ship's Cap Table

CFOs are making uncertainty a line item.

A few years ago, I could crack a Miller Lite and go on about chasing top-line growth or how I once approved a $10M ARR forecast based on vibes and a Notion doc. Now? None of my CFO friends have the time, or even the appetite, for that. They’re too busy learning, unlearning, and relearning what finance needs to be in an AI-powered world.

Brex captured this shift in The CFO Imperative, a survey of 500 finance leaders, and gives it to us straight. CFOs aren’t building for one scenario anymore, they’re building for 10.

69% say their stack is too complex. And with 97% seeing ROI from AI, they’re all but begging teams to adopt AI faster.

Bottom line: The new finance KPIs are flexibility at scale, global automation, and how fast you can deliver. See how they plan to make it happen.

We caught a rainy day on Nantucket, so as captain of my family’s fun boat, I forced everyone into a museum visit. Don’t worry, I bought them ice cream afterward, plus a slime toy for my three-year-old that later destroyed the tablecloth at a nice restaurant.

I’ve been obsessed with the whaling economy after finishing In the Heart of the Sea by Nathaniel Philbrick. It’s the story of the Essex, a whaleboat that is attacked by a large Sperm whale in the South Pacific who decides to ram their boat into oblivion.

The men are forced to abandon ship into three small life rafts with virtually no supplies. And you can guess what happens next, without any DoorDash available.

Only 8 of the 20 men survived, going more than 90 days adrift at sea. 3 months. Roasting in the hot sun. Hungry and thirsty. Aimlessly bobbing in the water.

Many of you may recognize this as the series of events that inspired Moby Dick.

The book also covers the economic modalities of the whaling industry in Massachusetts.

Like CT was propped up by GE in the 1990s, the island and eastern seaboard was propped up by whaling.

The museum guide showed us the cap table, or rather, the funding docs, from the whaleship Edward Cary. Think of it as the 19th-century version of a high-risk, high-reward startup. In the 1840’s, she pulled off six profitable voyages, each led by a different captain.

Her org chart was lean but specialized: captain (a professional PE backed CEO), three mates (VPs of product / eng / sales), boatsteerers (call them your SDRs), plus a few “ops” folks like a cooper, blacksmith, cook, and steward (head of FP&A). The crew was diverse, including New Englanders, African Americans, Native Americans, and seasoned sailors from Cape Verde and the Azores. And despite their ethic differences, everyone pulled in the same direction because the compensation plan was the same: rev share.

There was no salary. Everyone got a “lay,” or a fixed percentage of the revenue from the voyage. The captain’s cut might be 6 to 8 percent, while a cabin boy (who had to literally climb naked into the dead whale’s head to scoop the oil out) might get one four-hundredth (he should have negotiated better).

One of the perks of making this my full time job is, like a total weirdo, I have the bandwidth to rebuild it in excel (thanks, goal seek):

In today’s inflation adjusted terms, the total revenue was about $1.1 million. About 1/3 went to the crew, risking their lives and leaving home for years at a time, and 2/3’s to the boat owner and investors.

The Stock Holder’s Agreement was investor friendly AF. Worse than startups paying for their VC’s legal fees during a fundraise, ship mates had to pay for their own rations using their future expected payouts. And if they under estimated their needs, the price of goods went up by like 7,000% after you left the harbor. It wasn’t uncommon for crew mates to go negative on their future earnings because they needed more food.

If the ship came home with full barrels, you got paid what you were allocated on the cap table, less your rations. If it limped back empty (or you crashed and ate each other), you still owed the ship’s owner for your food (unless, of course, you got eaten).

Aside from the incentives and pay structures, I was fascinated by how the industry evolved, and eventually collapsed. It paralleled how many of us have gone about our careers, innovating within our companies to survive industry shocks, and sometimes changing sectors all together when the grass is greener.

The whaling economy started off as a scrappy side hustle, after the locals discovered the soil of Nantucket is shit and they couldn’t farm much. They would throw a guy in the equivalent of a lifeguard tower and when he saw a whale spout, he’d call down to his friends on the beach below to get in their row boat and haul ass. When they got one, they’d drag it back to shore and make it into oil.

But as they wiped out all the surrounding, slow moving Right Whales, they had to push further and further out to sea in search of a new product. That’s where they found the 10x more profitable (and 10x more dangerous) Sperm whales, who’s oil burned much longer and brighter. But as a result, the trips went from lasting a couple of hours to a couple of years. Many went as far as South America and the Arctic Circle.

As Nantucketers were moving upstream to the Enterprise they needed to build larger and larger ships to carry enough food for the journey and to hold the proper equipment to harvest the whales on board.

In this sense, necessity was the mother of invention, giving birth to an entire boat making economy in New England to support the whalers, much like chip makers and cloud providers today.

But it didn’t last forever. The whaling economy in Nantucket collapsed for three reasons:

The Cary was abandoned upon arrival in San Francisco by the eager gold miners. And that was the end of the Nantucket whaling industry.

It was a reminder of several maxims of business:

Private equity’s average holding period isn’t just stretching—it’s bursting at the seams.

Globally, buyout holding periods peaked at 6.6 years in 2023, according to Bain. But in North America, the average climbed even higher—to 7.1 years, the longest since at least 2000 (S&P Global).

Even with some easing in early 2024—median hold times fell to 5.8 years—we’re still well past the old 3–5 year playbook. The era of quick flips is fading.

And as an operator, that changes your job.

A convo with Ethan Schechter (former Snyk)

Are you building a sales org from scratch?

Or rebuilding one in the middle of an AI boom?

If so, this episode is your field guide. I sat down with long time friend and former co worker Ethan Schechter, SVP of Global Sales and Customer Success at Qodo (and the guy who helped take Snyk from $0 to $100M+ in revenue). We talked about the wild days of early-stage sales leadership. Ethan shares:

Oh, and most importantly, the episode ends with an entertaining roast of LinkedIn’s cringe posts, from fake ARR math to self-given nicknames and beyond.

Wishing you scalable unit economics from day one,

CJ