In 1997 at the age of 25, Robert opened his first restaurant, a large-format, dual concept called Buffalo Billiards & Havana Lounge in Nashville, launching what would become a lifelong career in hospitality.

Punch Bowl Social was conceptualized and founded by Robert after an extensive career conceptualizing and operating both large-format eatertainment brands and independent boutique restaurants.

Following the award-winning openings of nine different restaurant concepts, Robert began to actualize his vision for Punch Bowl Social in early 2010, opening the first location in Denver's historic Baker neighborhood in 2012. With lines around the block starting on day one, it was clear that Punch Bowl Social had struck a chord with young diners and drinkers seeking something authentic and out-of-the-ordinary. Robert opened 20 locations and elevated 2019 sales to $119m.

In 2017, Robert brought in premier PE firm L Catterton, and in 2019 transacted L. Catterton out with a new strategic partner, Cracker Barrel (NYSE: CBRL), at a $185m enterprise value.

In 2017, Ernst & Young recognized Robert as Entrepreneur of The Year® award. Robert's Punch Bowl Social brand earned a number of awards and recognitions, including Fast Company Magazine's 50 Most Innovative Companies in the World 2019, Nation's Restaurant News' 2018 Hot Concept, the 2019 Denver Business Journal Most Admired CEOs in Denver, and Nation's Restaurant News' 2017 Next 20 Brands to Watch, and a 2015 Breakout Brand.