My Parents Texted Me, “Don’t Come To Our Wedding Anniversary Party. Only ‘Proper’ Guests Will Be There.” So I Stayed Alone In My Apartment And Let Them Have Their Picture-Perfect Night Without Me. But That Same Day, My Sister Called, Voice Shaking, And Blurted, “Why Did You Hide This From The Family? Mom And Dad Just Saw The News And…”

I felt the old pull, the word family, the guilt that came with it. I told myself it was harmless— a few conversations, basic explanations, nothing that touched what I was really working on.

“Okay,” I said. “I’ll help.”

Caitlyn texted me the next morning.

“This means a lot. Come to the marina Saturday. We’ll go over it.”

I drove down. The office smelled like salt and fresh varnish. Caitlyn hugged me when I walked in—quick, professional, the kind of hug she gave clients. She led me to the conference room with the long table and windows overlooking the docks.

Yachts bobbed in their slips, white hulls gleaming under the sun. She sat across from me, leather notebook open.

“Tell me how this stuff works,” she said. “The pricing, the analysis.”

I kept it surface level. I talked about how data from photos could detect wear on gel coat, how market trends could predict depreciation, how algorithms could compare similar vessels across regions. I showed her sample outputs on my laptop—numbers, charts, nothing proprietary, no code, no backend, just concepts.

She leaned forward, eyes bright.

“This is perfect. Investors will eat this up.”

She took notes furiously. I noticed she wrote down phrases I hadn’t said out loud before—threaded valuation layers, a term I’d used in my private notes. I brushed it off. Maybe coincidence.

Two weeks later, she called.

“I need you at a pitch meeting. Just sit in the back. Be available if they ask questions.”

I went. The room was full of Boston money—suits, expensive watches, people who bought yachts the way other people buy cars. Caitlyn stood at the head of the table, clicking through a slide deck.

“Whitaker Yachts is leading the industry in data-driven valuation,” she said. “We’re using advanced analytics to deliver real-time accurate pricing that no one else can match.”

The slides had my frameworks, my terminology, my sample charts—cleaned up, but recognizable.

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