Find Your Freedom: Lessons from The Annual Toast Kickoff

Restaurants don’t fail because of the food. They fail because of broken systems.For years, the industry accepted a hard truth: to be successful, you had to be the glue holding a fractured business together. That meant working IN your business instead of ON your business. The rhythm of a restaurant is a double-edged sword. When it’s working, it’s a symphony. When it’s not, it’s a slow-motion car crash that demands every ounce of your focus, your energy, and your time. The manual heartbeat of a machine that should be running itself.I was just at in Orlando for the Toast Annual Kickoff, and I realized that the narrative of restaurant ownership is changing. Michael Ungaro from San Pedro Fish Market and Restaurant and Kings of Fi$h on Amazon Prime summed it up best from stage at the event. He said one word should be the focus of all service providers in hospitality: giving owners back their FREEDOM. Toast is intentionally building an ecosystem designed to help operators earn back the one thing that has become a luxury in hospitality: the freedom to actually run a business instead of being trapped inside it.I saw this in the diversity of the people in the room:* Global Pillars: Brands like Uber Eats and Coca-Cola, who bring the gravity and distribution of the world’s biggest stages.* The Next Wave: Startups like Palona AI, who are building the future with a speed and creativity that challenges every old assumption we have about “how things are done.”* Solution Partners: Service partners like F3 Tech, who are on the ground making sure the solutions actually hold up when the kitchen is slammed and the stakes are real.When technology companies, operators, and builders stop working in silos and start building together, the friction begins to disappear. And when the friction disappears, you get your life back.Leadership That Stays Close to the HeatOne of the most telling moments of the kickoff happened off-stage.Spending time with Aman Narang, Co-Founder and CEO of Toast, reinforced why this company feels different. Aman doesn’t lead from a 30,000-foot view. He is gritty. He believes in staying “uncomfortably close” to the product, the customer, and the problems.That mindset is why Toast supports 156,000 locations (as of Q3 2025). It’s not an accident. It’s a result of leadership that still remembers what it’s like to solve a problem on a busy Friday night when the house is full and the pressure is on.I saw that same human connection in Kelly Esten, Toast’s CMO. In an era of corporate polish, Kelly is practicing what we call Digital Hospitality. She isn’t just running a marketing department; she’s building a personal branded channel to spotlight the people behind the business. She understands that in 2026, the brands that win aren’t just “providers”—they are participants in our community.Documenting the IndustryAt Cali BBQ Media, our mission for our Toast partnership is simple: Tell the stories of the people who are building a better way.We are looking for the Toast partners who are helping operators reclaim their margin and their sanity. We want to find the restaurants that are scaling without losing the heart of what made them special in the first place.Restaurants don’t usually fail because of the food. They fail when the owner runs out of gas because they’re too busy being the “connective tissue” for the machinery of the business.We went to Orlando to see the future. What we found is that the future isn’t just about better code—it’s about giving people their freedom back.This is digital hospitality. And we’re just getting started.-Shawn Walchef @shawnpwalchefAt Cali BBQ Media, we’ve always operated on a simple, hard truth: if you don’t own your story, someone else will. That’s why I am so incredibly fired up to announce that we have officially signed a long-term storytelling partnership with Toast. It’s about a shared mission to document the most important shifts happening in our industry.We are officially on the hunt for the absolute best restaurants, the grittiest operators, and the tech innovators who are using Toast to start being the leaders they were meant to be. We want to tell the stories of those who are scaling their business and improving the guest experience without losing their soul in the process.Are you a Toast partner with a story to tell? Or an operator using the ecosystem to grow? We want to hear from you. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit restauranttechnology.substack.com