Cherry
Luke identified a massive inefficiency in the online travel marketplace: accommodation businesses were bleeding money through exorbitant commission fees (up to 30%) paid to OTAs like Expedia and Booking.com, while consumers had no way to book directly and get better deals. The core insight was that both sides had incentives to bypass the middleman—hotels wanted to avoid massive commissions, and customers wanted savings.
Cherry launched as a simple but powerful Chrome extension that sits on top of OTA websites. When a user searches for a hotel on Booking.com or Expedia, the extension pops up and shows them a direct booking deal with the property, complete with guest details, check-in/check-out dates, and promo codes pre-filled for frictionless checkout. Luke designed the product to work across hotels, resorts, and vacation rentals, with plans to expand into flights, attractions, and car rentals.
Instead of trying to acquire individual users directly, Luke took a B2B approach by partnering with hotels. He realized hotels would enthusiastically promote Cherry to their loyalty members because it let them reduce OTA dependency. One Canadian launch partner alone had 2 million loyalty email subscribers. This partnership model proved far more effective than paid acquisition, with YouTube and Reddit ads providing supplementary reach at $2-3 per install (down from $10-12 on Facebook/Instagram).
The partnership channel worked exceptionally well—hotels became distribution channels themselves. Paid media proved challenging at scale due to high CAC, but YouTube showed promise. The model is fundamentally sound: hotels save 30% on commissions by paying Cherry's $10/month + $0.79/click, and customers get discounted rates. However, investors questioned whether hotel loyalty members would actually install an extension for infrequent travel, and whether hotels would truly spam their members repeatedly to drive adoption.
In just four months, Cherry had signed nearly 1,000 partner properties across Australia, New Zealand, and Canada from major hotel brands. They were on track to launch in the US with 20,000 expected partners by November. Despite the traction, both Sam and Sean passed on the opportunity, skeptical that the travel industry's cutthroat economics and low booking frequency would ever support a standalone extension business—even though the unit economics appeared sound.
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