s·Term SheetTravel guru The Points Guy wants to revamp the luxury travel points system with JourneyBy Leo SchwartzBy Leo SchwartzReporterLeo SchwartzReporterLeo Schwartz is a reporter at Fortune covering fin, crypto, venture capital, and financial regulation.SEE FULL BIO Journey raised a $7.7 million seed round co-led by Lerer Hippeau and Slow Ventures.Courtesy of JourneyPoints fatigue is real.
What started as a nice-to-have bonus for traveling has ballooned into a sprawl of rewards grams 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 blem to care , but I’m sure plenty of this ’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 entrepreneur, Sutton met Kelly while serving as the chief digital officer at Red Ventures, a media-focused investment firm that owns brands Bankrate, Lonely Planet, and eventually, The Points Guy.
When Sutton left his role in 2021, he took a couple of years off to play fessional volleyball before figuring out his next venture.
After exploring the idea of in short-term rentals Airbnb perties, he had the idea of building out a loyalty gram for travelers.
After consulting with Kelly, he realized there was a broader blem—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 gram that people are excited .” Journey’s website looks a cross between a travel platform Booking.com (an online travel agency, in industry parlance) and an Instagram , with lush snippets of desert hideouts and jungle treehouses.
On the backend, Journey’s small team curates perties, now totaling more than 1,500 from around the world, that want to participate in their loyalty gram—a combination of independent hotels and rental perties.
Sutton says they’re not looking for certain price points (with perties 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 two cents, equating to a 10% rebate, which can be instantly redeemed during stays.
“Our gram is engineered so that you’re not being taken advantage of,” Kelly said.
Journey is the type of consumer-forward, design-first duct 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, whether they’d prefer to be greeted with red wine or mineral water, to help perty managers customize the experience.
And Journey is also building out a platform for influencers Kelly that matches them with perties. Eventually, the goal is to build out AI agents that will help tourists.
Sutton says it will make platforms Expedia, where you find a hotel by ing for the top 10 hotels in Paris, look antiquated. “Travelers will be on a trust journey with us,” he told me.
Leo SchwartzX: @leomschwartz: leo.schwartz@fortune.com Submit a deal for the Term Sheet here. Joey Abrams curated the deals section of today’s . here.
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Financial terms were not disclosed.FUNDS + FUNDS OF FUNDS- Dextra Partners, a New York City-based private equity firm, raised $825 million for its seventh fund focused on middle-market companies.- CRV, a San Francisco and Palo Alto, Calif.-based venture capital firm, raised $750 million for its 20th fund focused on seed and Series A rounds.This is the web version of Term Sheet, a daily on the biggest deals and dealmakers in venture capital and private equity.
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