Ever since moving to New York and freelancing, I’ve worked out of a co-working space, which is now where we work on Cushion. Our co-working space is more of a tight-knit community than a rent-a-desk situation, so we all eat lunch together. Lunch is very important at our space—we even have a #lunch-train Slack channel to plan our lunches and handle reimbursement.

Occasionally, someone has a great idea for lunch, which has become known as “adventure lunch”. On a typical day, we’d pick up food from a nearby place, order delivery, or bring leftovers from home. Adventure lunch is when someone suggests going to a restaurant that involves a long walk or ride on the subway—it’s a real treat and a great way to close out a long week.

An extension of the adventure lunch is what we call the “executive lunch”. We have a few small companies at our space among a wider group of freelancers. Whenever one of us is taking an executive lunch, it’s simply an adventure lunch that’s business-related. Recently, Cushion took its first-ever executive lunch.

Larry and I rode the subway to DUMBO, walked past our old building at 10 Jay St, and ended up at the finest restaurant for a business meeting—Shake Shack. We talked about our upcoming plans for Cushion, discussed how everything’s been going, and brainstormed what we could do to improve. We also made the mistake of ordering double burgers, cheese fries, and milkshakes. Larry had the brilliant idea of skipping a few subway stops, so we could walk off the extra pounds. We arrived back at the studio and got back to work.

I’m writing about this because I started my career in the corporate tech world where team dinners were at fancy restaurants—the kind of place I’d never dream of going with my own wallet. If we were with an exec, they would order for the entire table and only half of it would get eaten. The free-flowing drinks would catapult the bill into the thousands.

I think about this a lot now, and even though we have funding, I’m still running Cushion the way I ran it when we were bootstrapped—the only difference is that we can now afford to hire more people. We don’t need to live beyond our means when something can be expensed. We can have just as good a time at our favorite burger spot.