From Silicon Valley to the Diamond District: How a Tech Founder Proposed with a Custom Cushion Cut Ring
When a young tech CEO decided to propose, he didn’t go to Paris or Bora Bora. He flew to Manhattan’s Diamond District to design a cushion-cut engagement ring with a hidden halo — and walked out with more than just a “yes.”
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Jason Lin, a 29-year-old founder of a fast-growing AI startup, isn’t a celebrity. But last spring, he became a viral TikTok sensation when he proposed to his girlfriend in Dumbo, Brooklyn, with one of the most intricate engagement ringsviewers had ever seen.
What most people didn’t know was that the journey started weeks earlier — inside a small booth at 44 West 47th Street in New York City’s Diamond District.
Jason had been researching jewelers for months. “I wanted something that wasn’t just sparkly — it had to feel intentional, symbolic,” he explained. He ruled out chain stores and generic settings, landing instead on a boutique that specialized in custom engagement rings, lab grown diamonds, and vintage-style craftsmanship.
Designing the Ring: Meaning in Every Detail
With the help of a master setter, Jason opted for a 3.00 carat cushion-cut lab-grown diamond — colorless, VS1 clarity — framed in a hidden halo of micropavé stones. The band featured a split-shank design inspired by his and his fiancée’s initials curving together.
Instead of platinum, they chose 18k rose gold for a warmer tone against her skin.
“Even the under-gallery had filigree work,” Jason said. “Nobody else will see it, but she will. That’s the point.”
But That’s Not All…
Before leaving NYC, Jason walked next door and bought himself a pre-owned Patek Philippe Calatrava — a classic dress watch he’d dreamed of since college.
“It felt like a full circle moment,” he said. “I built the company, found the girl, and now I have the timepiece to mark the milestone.”
The store, known for sourcing pre-owned watches and custom jewelry, handled both the ring and the Patek. Everything was appraised, boxed, and shipped back to San Francisco in time for the proposal.
The Proposal: Simple and Perfect
A week later, Jason proposed on a rooftop overlooking the Brooklyn Bridge. The ring caught the golden-hour light — and the moment was captured by a stranger who posted it to TikTok, where it racked up 1.2 million views in 48 hours.
“I said yes before he even opened the box,” his now-fiancée later joked in the comments.
Why More Entrepreneurs Are Choosing Custom
Jason’s story isn’t unique anymore. More young professionals — especially in finance, tech, and design — are choosing bespoke jewelry and investment watches over off-the-shelf options.
The NYC Diamond District is still where deals happen. Not just proposals, but legacy pieces. A place where engineers and CEOs can design with intention — and wear the result forever.