The making of the “In Case of Deal, Break Glass” box
The $10M Pen Stroke
First, the origin story. The year is 2012. I’m a decade deep into redefining the traditional menswear experience, while simultaneously running a two-year pilot of a private social club concept inside a former barbershop. After months of negotiations, I was set to sign a 10-year lease on 22,000 square feet of historic San Francisco real estate for Wingtip. At $80,000+ a month (plus built-in escalations), this was a $10 million high-wire act. Naturally, I brought my own fountain pen and inkwell. Big deals deserve big ceremony.
April 2012: signing the biggest deal of my life.
Years later, I realized a lot of the members of my club also had big deals they were doing: building purchases and sales, fundraising rounds closed, and mergers and acquisitions—and they, too, should be able to make a ceremony out of a signing. I created a shabby v1.0 of the deal closing box in the club’s Boardroom. It was used once by an investor who was buying an expensive new home.
Five years passed before the idea resurfaced during a 6sensory Supper for 6sense. The ultimate flex for an executive dinner? Getting a guest to close a deal mid-meal. But pulling up a DocuSign link over fine dining is an absolute mood-killer. If you're going to ask an executive to sign on the line that is dotted between courses, make it unforgettable. Punching a fist through breakaway glass to retrieve a vintage fountain pen? Now that’s a closer's ritual.
I needed a travel version of the “In Case of Deal, Break Glass” box. Lucky for me, my father-in-law is an extremely talented woodworker. This box is one of the easiest and least beautiful things he’s made (as my kids can attest given their collection of beautiful, handmade wooden toys from their Silly Pa). Now, the pictures below don’t show how much I helped because I was the one taking the pictures, but I promise I did help.
The key feature of the Deal Closing box that makes it different from a regular box is that you need a channel through which you can slot a pane of Hollywood breakaway glass (aka sugar glass) for the guest to punch through. You can see the channel best in the 3rd photo from the right, top row.
Road-testing the Breakaway Glass
The box made its inaugural appearance at a 6sense 6sensory Supper at Spruce, a Michelin-star restaurant in San Francisco. Below are photos of Rob Giglio, at the time the Chief Customer Officer at HubSpot but also the former CMO of DocuSign (the electronic signature company) breaking the glass and signing a deal between HubSpot and 6sense. Since I attend to every detail, the fountain pen and ink were teal, 6sense’s primary color. And since I believe strongly in souvenirs, Rob got to keep the pen as well.
The Field Marketer’s Takeaway
Digital speed is great for scale, but enterprise sales run on emotion, trust, and momentum. There are some late-stage deals that you can close faster if you treat the closing like a ceremony, rather than an administrative chore. The photos speak for themselves: this deal-closing shattered expectations.
