Journey 🏨

Opening Remarks

This week, I was chatting with a founder building something wildly original—and struggling to raise. It reminded me of a strange truth: the best startups often have the hardest time fundraising.

Airbnb was laughed out of rooms. Uber was passed on by notable of VCs. Novelty doesn’t scan well in spreadsheets, and most investors don’t bet on what they don’t understand. But that’s exactly where the magic is.

I’ll be diving deeper into this in an upcoming LinkedIn post (follow me to catch it). In the meantime, if you have a story of a great company getting passed on, hit reply and let me know. Now, onto this week’s feature:

Bulletpitch’s publication covers the hottest early-stage startup before being picked up by larger media outlets. If that’s you, apply here.

Setting the Scene

• Independent hotels and short-term rentals are losing up to 30% of their revenue to OTAs like Booking.com and Airbnb, cutting into margins and weakening the direct guest relationship.

• Meanwhile, major hotel chains (think the Hiltons and Marriotts of the world) are thriving by leveraging loyalty programs to drive repeat, direct bookings — boosting profitability while keeping guests coming back.

• Independent properties, despite offering high-touch, memorable experiences, often lack the infrastructure and scale to compete — leading to low retention and a growing dependence on third-party platforms.

• This week’s company offers a universal loyalty platform built exclusively for independents — empowering them to join an alliance of properties, boost retention, increase direct bookings, and ultimately take back control of the guest relationship.

In a Sentence

Journey is a loyalty platform for independent hotels and private rental homes, offering the rewards power and guest insights of big chains — without sacrificing the individuality that makes them special. 

• Loyalty Platform: Independent hotels and short term rentals join the Journey Alliance, gaining access to a SaaS platform that enables automated point issuance and redemptions, while allowing guests to earn and redeem points across a unified network of stays.

• Power: Guests earn significantly more points when booking direct, giving them a compelling reason to bypass OTAs and deepen their connection with the brand.

• Insights: Operators gain access to data-driven insights that power hyper-targeted marketing, personalized offers, and curated guest experiences—turning one-time visitors into loyal return guests. 

The Basics

• Industry: Travel SaaS, Loyalty Programs

• Headquarters: New York, NY

• Year Founded: 2024

• Employee Count: 8

• Investors: Slow Ventures, Brian Kelly, Chris Burch, James McBride, Eric Wu, 1528 Investments, and various other angels.

• Amount Raised: $5.25M

• Business Model: Point issuance fees, redemption fees, co-branded credit card interchange, and a few other revenue streams.

• Early Traction: Click HERE to see all the hotels who have already joined the alliance.

Sponsored Content*

IN PARTNERSHIP WITH

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Weekly Feature Continued

Due Diligence

WHAT WE LIKE

• Market Opportunity: The global independent hotel and STR market is worth approximately $350B, yet independent operators—despite being larger in aggregate than top hotel chains—lack the scale to compete individually.

• Go-To-Market & Value Proposition: With 2025 expected to be a record year for travel, Journey is well-positioned to serve the ~77% of European hotels and 40% of U.S. properties that operate independently and typically lack loyalty infrastructure.

• Network Effects: As more properties join the Journey Alliance, the value of the platform compounds—exposing more travelers to the ecosystem and driving greater adoption, engagement, and direct bookings.

POTENTIAL RISKS

• Adoption Risk: Journey’s success partially hinges on consumers consistently claiming their points.

• Competition: Although Journey isn’t directly competing with OTAs, they do face competition from the well-established loyalty programs of major hotel chains.

• Economic Sensitivity: The travel sector is highly vulnerable to macroeconomic downturns, which can impact demand and spending.

Founder Profile

• John Sutton, CEO: Previously CDO of Red Ventures.

• Matt McBride, CFO: Previously CFO of Buildcasa.

Comps

• The Leading Hotels of the World 

• Relais & Chateaux

Event Board

• Seed Round Supper, NYC: On April 10th, we are hosting a 3 course meal in a stunning NYC penthouse for founders (Pre-seed-Series A). Apply HERE.

• Tech Carnival NYC: On June 3rd, we’re bringing our famous Tech Carnival to NYC. A bigger announcement is coming soon—but early birds can sign up HERE.

• Founding GPs Dinner NYC: On June 5th, we’re co-hosting a curated and intimate dinner for founding GPs and emerging managers. A bigger announcement is coming soon—but early birds can sign up HERE.

Note: Spots are limited for dinners. If you apply and aren’t approved for a dinner, we will try to get you to a future event.

Cast Your Vote

Last Week Today

• The Results Are In: Avant Health, an AI-native benefits administrator replacing TPAs and their outdated tooling stack to help employers offer smarter, cheaper, more personalized healthcare plans.

• Subscriber Feedback: “This is brilliant, Avant’s AI-native platform delivers the compliance, cost control, and scale that legacy TPAs can’t.”