The making of the “In Case of Deal, Break Glass” box
First, the inspiration. It’s 2012, I’m a decade into my dream of redefining the traditional menswear store having piloted a small private, social club addition to it for two years. After months of back-and-forth, I’m about to sign a 10-year lease on 22,000 square feet of retail and office space in a national historic landmark building in downtown San Francisco for Wingtip. With rent of $80,000+ per month with built in increases, this was a $10M commitment I was making. I arrived with my own fountain pen and inkwell to treat the moment with the seriousness it deserved.
Me, in 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, 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.
A good five years passed and I hadn’t thought about it much until I started doing the 6sensory Supper executive dinner for 6sense, an account-based marketing software company. I thought, the ultimate, proof of my salesmanship would be a guest signing a contract during the dinner! But a Docusign would be so anti-climactic; if I’m going to ask someone to sign a contract during a dinner, it has to be the most memorable contract-signing of their life. Putting their fist through glass (fake glass, yes) to get ritualistic writing instruments to sign with would do it.
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.
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.

