5 Lessons I Learned From Interviewing the Top CEOs in Hospitality

**Running a restaurant will consume you if you get trapped in the daily firefight.** Between broken ice machines, labor shortages, food cost spikes, guest complaints, and vendor delays, it is easy to spend 100% of your energy just trying to make it to last call. At Cali BBQ, we’ve been grinding on the restaurant side for 18 years. On the media side, we’ve been at it for almost a decade. And for the first 5 years of running Cali BBQ Media, we made zero dollars. It wasn’t until we figured out how to build real digital hospitality and monetize media that we started securing major brand partnerships with companies like Toast, Pepsi, Restaurant365, Uber, Google, and Ring. The top leaders in hospitality do not just survive the day. They play the long game. Restaurant owners cannot afford to think like traditional restaurant owners anymore; we have to operate like media companies, technology adopters, and community builders. Here are five hard-earned lessons from sitting down with the CEOs, founders, and operators shaping the future of our industry. **1. Dream Big (And Stay Grounded on the Floor)** If you want to access the top minds in your industry, you have to be willing to pitch a vision that sounds ridiculous to average thinkers. When Cali BBQ switched point-of-sale systems from Aloha to Toast in 2020, I told Will Eppard, Toast’s sales director in San Diego at the time, that I was going to interview the cofounders of Toast. He laughed. Because at the time, it sounded absurd. We were a local BBQ joint running a media experiment that hadn’t generated a dime in profit. Two years later, after interviewing then-CEO Chris Comparato, I was invited to speak on a customer panel in front of 1,300 Toasters at their sales kickoff. Right after that keynote, I sat down with co-founder Aman Narang (now CEO) to record an episode of *Restaurant Influencers*. That moment started with a massive goal and years of small, daily actions. What stood out from Aman was the mindset behind the tech: the best technology leaders obsess over their customers’ problems. Toast was built by founders sitting inside restaurants, watching ticket bottlenecks in real time, and writing code to solve operational pain points. Dream as big as possible, but stay obsessively close to the operator. **2. Play the Long Game (Relationships Compound)** The high-value interview, the strategic partnership, or the major brand deal almost never happens on the first ask. It often doesn’t happen on the second or third ask either. Sometimes it takes 25 touchpoints across multiple years. When we went heavy into ghost kitchens during the pandemic, we took major risks. Through that entire buildout, I told the team at CloudKitchens that eventually I was going to sit down with Travis Kalanick, co-founder of Uber and founder of CloudKitchens, to talk about why a barbecue brand was building a media company. Eventually, it happened. Travis didn’t just grant the sit-down, he turned the tables and interviewed me in front of his entire CloudKitchens all-hands team. That door opened because we stayed consistent when there was no instant payout. In media, tech, and restaurants, trust compounds over time. Keep showing up, keep getting better, and play the long game. **3. Real Leaders Want to Share the Struggle** One of the biggest misconceptions in business is that top-level CEOs are completely unreachable. Some are guarded, but the most impactful leaders actually want to share their origin stories, their struggles, and what they’re building. That was my experience with Jordan Boesch, co-founder and CEO of 7shifts. We originally reached out because our restaurant needed to upgrade from legacy scheduling software like HotSchedules to a modern, cloud-based workflow. That initial operational reach-out turned into Jordan appearing on *Digital Hospitality*, *Rising Tides Live*, and Restaurant Influencers published by Entrepreneur Magazine. We’ve reconnected in person multiple times at the National Restaurant Association Show in Chicago. What makes Jordan stand out is his openness. He regularly talks about product missteps, hard customer feedback, and the relentless work required to scale software. Great leaders are always seeking raw feedback from operators in the trenches to build better products. **4. Earn Visibility Before You Need It** Nobody starts on the keynote stage. Everyone starts small, makes embarrassing mistakes, and figures out the playbook on the fly. Look at Troy Hooper. Before building Kiwi Restaurant Group and scaling Pepper Lunch across North America as CEO of Hot Palette America (and now Strategic Advisor to the Board), he was showing up daily on Clubhouse during the pandemic. He was giving away advice for free, testing ideas, and building relationships on LinkedIn and Instagram before the massive expansion deal was ever on the table. Now he hosts his own show *The Pineapple Perspective* and shows up weekly on Rising Tides Live. Modern leadership is not granted by a title on a business card, it is earned by showing up consistently before anyone gives you a platform. Be visible, be useful, and build in public long before the crowd arrives. **5. Build Your Own Media Engine** The single biggest lesson from interviewing world-class hospitality leaders is simple: Great leaders create their own media. They stop waiting for local newspapers, food critics, or trade magazines to tell their story. They build the digital infrastructure themselves. If you do not control your narrative, third-party delivery apps, review sites, and algorithms will control it for you. Omnichannel content (short-form video, podcasts, LinkedIn updates, YouTube series) is how you build trust at scale. Media is how prospective franchisees understand your vision. It is how top-tier talent discovers your culture before applying. It is how vendors, investors, and guests connect with your brand before ever stepping through the front door. The difference between good operators and industry-defining leaders is not that leaders have secret answers. It is that they are better at asking hard questions, telling honest stories, and staying visible long enough for scale to find them. That is how a single barbecue restaurant in San Diego transformed into a media company. That is how cold DMs turned into key partnerships, and how those partnerships turned into brand revenue. If you’re an operator navigating tech shifts, bad leases, or figuring out how to build your brand online, reach out on DM **@Shawnpwalchef**. **Stay curious. Get involved. Ask for help.** -Shawn 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