Episode 633: From Bourbon Street to Benefits: Keith Santangelo on Serving Restaurants in a New Way

Keith Santangelo joins Wil in-studio to trace his journey from growing up in a Cajun-Italian butcher/grocery family in Baton Rouge to owning New York City restaurants, leading major restaurant groups, and now serving independents through AccessWave. They reminisce about Keith being one of Schedulefly’s earliest customers, talk about the magic of independent restaurants as “third places” (with Seinfeld’s diner as a touchstone), and unpack how the industry’s resilience showed up during COVID. Keith walks through selling his Hell’s Kitchen spots before the pandemic, stewarding scratch-kitchen concept Jose Tejas/Border Café through the shutdowns, then running operations and finance for Serafina’s global group and navigating licensing vs franchising abroad. From there, he explains why he pivoted from opening more restaurants to building an insurance and benefits solution specifically for hospitality, bringing a “unreasonable hospitality” mindset to a traditionally cold, transactional world. Throughout, they dig into tech overload, the adoption gap between shiny features and what teams actually use, the power of real implementation support, and why everyone should work in a restaurant at least once. The episode lands on family, balance, and why serving independent restaurants still sits at the center of Keith’s life and work.10 Takeaways Hospitality in the DNA – Keith’s love for small, family businesses started in his grandfather’s meat market and grocery stores, where he quickly gravitated to the front-of-house and guests. Independent restaurants as “home base” – From Seinfeld’s diner to neighborhood spots like Pie’s Eye, they’re the community living rooms where people gather, talk, and feel known. Early Schedulefly believer – Keith adopted Schedulefly around 2008 at Planet Hollywood, brought it to his own restaurants, and has stayed connected to Wil and the brand ever since. Owning and selling in NYC – He co-owned Bourbon Street Bar & Grill and Brazen Tavern in Hell’s Kitchen, later selling—partly to be more present with family—and, unknowingly, just ahead of COVID. How deals actually get done – Restaurant valuations often center on a multiple of EBITDA plus lease/liquor-license realities, but in practice many sales hinge on relationships and trusted partners. COVID as a resilience test – At Jose Tejas/Border Café, a 100% dine-in scratch concept with zero to-go, the team reimagined operations from the ground up and came out stronger. Scaling with Serafina – Running ops and finance for a 22-unit, $100M+ Italian group taught Keith the complexity of global growth, including why international licensing can beat franchising. The tech adoption gap – Many operators pay for enterprise tools but use a fraction of the features; if you’re only using 20% of the value, you shouldn’t be paying 100% of the bill. Hospitality belongs in “boring” sectors – With AccessWave, Keith is importing restaurant-style hospitality into insurance and benefits, aiming to be a true partner, not just a broker. Family as the why – Behind all the big roles and decisions is Keith’s desire to provide for and be present with his wife and four kids—while still serving an industry that “saved” so many lives.