Points fatigue is real. What started as a nice-to-have bonus for traveling has ballooned into a sprawl of rewards programs and arcane conversions that requires an advanced degree in statistics to manage.
Brian Kelly made a whole career off the cottage industry, parlaying a side hustle of maximizing credit card and travel rewards into a blog, The Points Guy, that became a verifiable franchise. Now he’s arguing that the points system has jumped the shark. Alongside Lerer Hippeau and Slow Ventures, he’s backing the New York-based startup Journey in a $7.7 million seed round to set it back on the right track.
Maybe this is too much of a first-world problem to care about, but I’m sure plenty of this newsletter’s readers were distraught when Chase announced an abstruse modification of their Sapphire Reserve credit card, or when Marriott acquired Starwood. Who doesn’t love fake internet money that can occasionally give you an airline upgrade or a free hotel night?
John Sutton, the cofounder and CEO of Journey, thinks the system needs a revamp. A longtime tech entrepreneur, Sutton met Kelly while serving as the chief digital officer at Red Ventures, a media-focused investment firm that owns brands like Bankrate, Lonely Planet, and eventually, The Points Guy.
When Sutton left his role in 2021, he took a couple of years off to play professional volleyball before figuring out his next venture. After exploring the idea of investing in short-term rentals like Airbnb properties, he had the idea of building out a loyalty program for travelers. After consulting with Kelly, he realized there was a broader problem—not only of short-term rentals and many independent hotels lacking the infrastructure to create rewards systems, but that points in general were increasingly broken. “They’ve been losing the magic of loyalty,” Kelly told me. “There’s a big opportunity to create a program that people are excited about.”
Journey’s website looks like a cross between a travel platform like Booking.com (an online travel agency, in industry parlance) and an Instagram feed, with lush snippets of desert hideouts and jungle treehouses. On the backend, Journey’s small team curates properties, now totaling more than 1,500 from around the world, that want to participate in their loyalty program—a combination of independent hotels and rental properties. Sutton says they’re not looking for certain price points (with properties ranging from several hundred to many thousand dollars per night) or stars, but whether they’ve “created something special that has a story to tell” (you can check out their portal, which just launched, to judge for yourself).
The upshot for visitors, Sutton and Kelly argue, is that the system is straightforward: You earn five points per dollar spent if you book directly through their platform, with each point worth about two cents, equating to a 10% rebate, which can be instantly redeemed during stays. “Our program is engineered so that you’re not being taken advantage of,” Kelly said.
Journey is the type of consumer-forward, design-first tech product that you don’t see much anymore—a simple concept executed with flair. But this being 2025, there is AI involved, of course. The company has built tools that track visitor preferences and behavior, like whether they’d prefer to be greeted with red wine or mineral water, to help property managers customize the experience. And Journey is also building out a platform for influencers like Kelly that matches them with properties. Eventually, the goal is to build out AI agents that will help tourists. Sutton says it will make platforms like Expedia, where you find a hotel by searching for the top 10 hotels in Paris, look antiquated.
“Travelers will be on a trust journey with us,” he told me.
Leo Schwartz
X: @leomschwartz
Email: leo.schwartz@fortune.com
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