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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VENTURE DEALS

- Tako, a São Paulo-based developer of AI agents that run payroll and workforce operations, raised $18 million in funding from Ribbit Capital, a16z, and founders.

- Raise Robotics, a San Francisco-based developer of a robot designed to complete construction tasks, raised $7.8 million in seed funding. MaC Ventures led the round and was joined by Undivided Ventures and existing investors Cybernetix Ventures, Zacua Ventures, and Union Labs.

- Qbeast, a Bellevue, Wash.-based data infrastructure company, raised $7.6 million in seed funding. Peak XV's Surge led the round and was joined by HWK Tech Investment and Elaia Partners.

- Pearl Edison, a Detroit-based general contractor for residential electrification and energy efficiency projects, raised $3.3 million in seed funding. New System Ventures and Commonweal Ventures led the round and were joined by Lightbank and Newlab.

- Neurogram, a São Paulo-based neurological diagnostics platform, raised $3 million in seed funding. Headline led the round and was joined by Romero Rodrigues.

PRIVATE EQUITY

- Machinify, a portfolio company of New Mountain Capital, agreed to take Performant Healthcare, a Plantation, Fla.-based payments company for the health care industry, private for approximately $670 million.

- New Mountain Capital agreed to acquire a minority stake in Wipfli, a Milwaukee-based advisory and accounting firm. Financial terms were not disclosed. 

EXITS

- MPLX acquired Northwind Delaware Holdings, a Houston-based sour gas gathering, treating, and processing services business, from Five Point Infrastructure for $2.38 billion. 

- Cinven agreed to acquire a majority stake in Smart Communications, a London, U.K.-based cloud-based enterprise customer communications, from Accel-KKR. Financial terms were not disclosed.

- NDT Global acquired Entegra, an Indianapolis-based premium integrity and inspection company specializing in Ultra-High-Resolution Magnetic Flux Leakage in-line pipeline inspection services, from Amberjack Capital. 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.