Hook, Line, and Term Sheet: Fishing for Capital and Reeling In Investors
A Fisherman’s Guide to Fundraising
Every day is a new day. It is better to be lucky. But I would rather be exact. Then when luck comes you are ready…It’s silly not to hope. It’s a sin.
—Ernest Hemingway
He said, “Throw your net on the right side of the boat and you will find some.” When they did, they were unable to haul the net in because of the large number of fish.
—John 21:6
Above: The Old Man and the Seed.
I’m lucky enough to spend my summers on a small spit of sand wedged between Jamaica Bay and the Atlantic.
Within the sea are fish, and where there are fish, there are fishermen.
Every sunrise and sundown, eager anglers plant their feet in the surf—backs straight, rods arced, eyes fixed—and they wait, they wish, they dream of landing their own Moby Dick or, at least, a respectable flounder or two.
This setting serves as inspiration for me. It has been the fuel that has fired passages like this:
To write is to wade, alone, into the vast, murky ocean of thought and idea. It is equal parts treading water and drowning, a haphazard stumbling toward insight and inspiration. It is plumbing into the depths of your soul, groping around to grab hold of something true and real and unique and you. It is casting and reeling, changing the tackle and hoping that the Big One doesn’t just nibble at your hook, but firmly latches on. And that you can successfully reel it in.
and pieces like this:
The same surf that teaches me to chase slippery sentences also hands out a PhD in deal-making. Out there, every cast is a pitch, every tug a term-sheet whisper. Watch long enough and you realize: fundraising is just fishing with revenue instead of a tackle box.
The Deck: The Hook
Shiny, barbed, baited, and purpose-built to spark curiosity—nothing more. A hook doesn’t fight the fish, it just convinces it to bite.
The Founder(s) and Team: The Fishermen
Skill, stamina, and stories of “the one that got away” lure capital as much as any spreadsheet. Investors back people who know when to yank, when to yield, and when to swap bait.
The Product & Business Model: The Rod and Reel
A cheap rod snaps under pressure; a jammed reel loses line. Your tech, traction, and unit economics need torque. Big fish test gear, so too do big checks.
When all three click, you’re rewarded with both a tense line and a shot of adrenaline that together produce an electric hum of possibility running from gill to elbow. Without it, you’re just a beach bum waving string at seagulls.
After years of watching both sides of this dance—founders casting, investors circling—I’ve collected some hard-won wisdom from the water’s edge. There are three essential, tackle box truths:
Small hooks land big fish. A five-slide deck beats a 50-slide opus every tide. Curiosity, not completeness, sets the hook (and nobody reads anymore). Less is almost always more in the attention economy
Change bait, not ocean. If they’re not biting, iterate the story before abandoning the market. Fishermen don’t curse the water, they swap lures
Meetings aren’t landings. A strike is thrilling, but until the fish hits the sand (i.e. signed term sheet, wired funds), keep the line tight and your eyes on the water
So the next time you polish your deck, picture yourself ankle-deep in foam as dawn pinks the sky.
Cast clean, feel the tug, and reel with intent.
With a little bit of luck, the right equipment, and a great deal of practice, you just might yell “Fish on!” as you reel one in.
Per my about page, White Noise is a work of experimentation. I view it as a sort of thinking aloud, a stress testing of my nascent ideas. Through it, I hope to sharpen my opinions against the whetstone of other people’s feedback, commentary, and input.
If you want to discuss any of the ideas or musings mentioned above or have any books, papers, or links that you think would be interesting to share on a future edition of White Noise, please reach out to me by replying to this email or following me on Twitter X.
With sincere gratitude,
Tom