Chet Pipkin built Belkin into one of the world’s largest technology companies, selling more than a billion products before founding Desolation Hotel. His approach to selecting and implementing hotel technology stems from decades of experience building tech products—but his framework is refreshingly straightforward.
“For me, this is really straightforward and it’s really simple,” Pipkin told me during a recent conversation on the Hospitality Daily Podcast. “It’s getting the objectives and it’s getting what matters to you right on that single page.”
That simplicity drives results. As a guest at Desolation Hotel, I experienced it firsthand—from the booking process to checking out a bike, every touchpoint felt effortless. For hotel operators struggling with technology decisions, Pipkin’s approach offers a practical framework worth adopting.
Start with a single page of objectives
The foundation of Pipkin’s technology philosophy comes down to clarity about what you’re trying to accomplish.
“So what is it we’re trying to do?” he asks. “Any place where there’s friction, we want to take the friction out. Anytime you’re going to encounter any kind of problem, we want to anticipate it and solve it for you before you have it.”
This single-page approach forces you to prioritize. You can’t list every feature you might want someday—you have to identify the problems that actually matter to your operation and your guests.
Accept that nothing solves everything
One of Pipkin’s most important lessons comes from acknowledging trade-offs up front.
“There’s always pluses and minuses and pros and cons to everything. Nothing solves everything. Just surrender that thought,” he says.
This thinking led Desolation Hotel to select Cloudbeds as their property management system. Pipkin acknowledges the platform has gaps in reporting and analytics compared to some alternatives. But the decision made sense based on their priorities.
“Cloudbeds is unbelievably easy for the team to use and for the support,” he explains. “And because it’s cloud-based, all of us can access it anywhere all the time.” The ease of use and accessibility mattered more than advanced reporting features.
Solve real problems, not imaginary ones
Pipkin sees a common mistake in technology implementation: solving problems that don’t exist.
“My own experience in tech has been far too often people are trying to solve a problem that doesn’t exist and actually create complication for folks,” he notes.
At Desolation Hotel, this meant carefully considering each technology addition:
- Agreements: A simple digital signature system.
- Communication: Text chat for guests wanting information.
- Entertainment: Connecting standard streaming services guests already use at home.
“The TVs work the way you probably use your TVs at home,” Pipkin explains. “It isn’t some hotel system you got to figure out. I use Hulu or I use Netflix… That’s the way you do it in your normal life.”
Don’t add features just to be clever
This might be the hardest discipline for operators to maintain—resisting the urge to add technology because it seems impressive rather than because it solves a problem.
“You take all the friction out, you put all the experiences in, and don’t add anything because you want to be cute,” Pipkin says.
Every technology addition should pass a simple test: Does this remove friction or create it? Does this solve a problem guests actually have, or does it create a new problem they have to figure out?
Technology must empower your team, not replace them
Perhaps the most critical insight is how technology should support—not substitute for—human service. When I mentioned my experience using the text chat late on a Friday evening, Pipkin emphasized the importance of that human element.
“The fact that there’s a person there is such a critical thing,” he says.
He shared a recent frustration trying to book additional nights at a major hotel brand. Despite his elite status, he couldn’t reach a person who could help. “When you call us or you chat with us, there’s a person,” Pipkin says. “Scale with people. Whatever you think you’re saving [by removing them], you’re losing.”
The “Dog Food” Test: Use your own systems
Pipkin has a simple practice that keeps him grounded in reality: he uses his own booking system as a paying customer.
“I always just use my own system. I pay for things. If I’m booking for friends, I go through and I book it myself because I want to know how we’re doing, what it feels like,” he explains.
Then he makes a pointed observation about leaders at major hotel companies: “They’re not booking their own rooms on their own system. They would never stand for it.”
Applying this framework at your property
Use your own systems. Book rooms, check in, and interact with your technology the way your guests do. If you find it frustrating, fix it.
Get your objectives on one page. What problems are you actually trying to solve? Force yourself to prioritize—if it doesn’t fit on one page, it’s not clear enough.
Accept trade-offs explicitly. No system does everything perfectly. Identify what matters most (e.g., ease of use vs. analytics) and choose accordingly.
Solve real problems. Be honest about whether you’re solving a real issue or just being clever.
Keep it simple for users. All the complexity should happen behind the scenes. If your guests need training to use something, you’ve made it too complicated.
Scale with people. Technology should empower your team to provide better service, not replace human interaction. Automate tasks, not relationships.
