
Travel guru The Points Guy wants to revamp the luxury travel points system with Journey
Key Takeaways
Inside the startup’s $7.7 million seed round led by Lerer Hippeau and Slow Ventures.
Article Overview
Quick insights and key information
6 min read
Estimated completion
cryptocurrency
Article classification
August 4, 2025
11:52 AM
Fortune
Original publisher
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
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 Investment and Elaia Partners.- Pearl Edison, a Detroit-based general contractor for residential electrification and energy efficiency jects, 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 apximately $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 cessing services , 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.This is the web version of Term Sheet, a daily on the biggest deals and dealmakers in venture capital and private equity. for free.
Related Articles
More insights from FinancialBooklet