Tomorrow's episode features a candid conversation with Kurien “KJ” Jacob, former Chief Commercial Officer at Highgate Hotels turned Partner at Highgate Technology Ventures.
Key Takeaways:
1. Unique Investment Model: Unlike traditional VCs, Highgate Technology Ventures invests partner capital exclusively in hospitality tech, validating portfolio companies through the Highgate ecosystem before investing—ensuring real-world testing and immediate customer feedback.
2. Why Startups Fail: "They run out of money. That's the number one reason." KJ's advice: focus on consistent performance year after year, not fundraising or exits.
3. Fragmentation as Opportunity: Hospitality's complexity—owners, management companies, brands, independents—creates a moat against outside capital that doesn't understand the nuances. This benefits those with deep industry knowledge.
4. High-Tech AND High-Touch: KJ envisions technology enhancing human connection, not replacing it: "Let's get back to the personality phase... like Cheers at your neighbor bar." Technology should eliminate the mundane, not the human.
KJ's journey from "firing himself" from a comfortable executive role to building an investment firm reveals a fundamental truth: comfort is the enemy of innovation.
Key Hospitality & AI News
The Sonder Collapse: A Cautionary Tale
The hospitality industry witnessed a dramatic implosion this week as Sonder Holdings, once valued at over $1 billion, abruptly ceased operations and filed for Chapter 7 bankruptcy liquidation. The company's demise came just one day after Marriott terminated their licensing agreement due to Sonder's default, stemming from costly and delayed technology integration challenges that resulted in significant unanticipated costs and sharp revenue declines. (Sonder to shut down after Marriott ends deal +2)
The human cost has been severe, with guests receiving immediate eviction notices—some told to vacate within 24 hours—creating chaos for travelers who had booked through Marriott channels. (One Mile at a Time) This marks another cautionary chapter in the SPAC boom's aftermath, with Sonder joining WeWork, 23andMe, and others in the graveyard of failed SPAC mergers. (Hoodline)
AI's Accelerating Impact on Hotel Operations
Recent research shows 58% of guests believe AI improves their booking and stay experiences (you best believe this will increase with younger generations), with 70% finding chatbots helpful for simple inquiries while still preferring human interaction for complex requests. (Hotel Tech Report)
The landscape in 2025 has shifted dramatically—AI is no longer an add-on but embedded as essential components of daily workflows. Platforms now offer AI-driven middleware that can automatically resolve system integration challenges, and no-code customization tools allow hotel teams to build custom workflows without technical expertise. (Hoteltechnologynews)
My latest book is "Co-Intelligence" by Ethan Mollick
Mollick's insights offer crucial strategic guidance, and I wanted to share a few with you:
The Jagged Frontier Principle: AI capability isn't linear—it excels at some complex tasks while failing at seemingly simple ones. In hospitality, this means carefully mapping where AI augments versus replaces human judgment.
Co-Intelligence, Not Replacement: The most successful AI implementations treat the technology as a collaborative partner rather than a replacement. Treat “AI like a human” team member.
The Invitation to Experiment: Mollick emphasizes that organizations must become "experimental machines"—constantly testing AI applications. Consider establishing sandbox environments where your hotel partners can safely explore AI capabilities without operational risk.
The Centaur Model: Like centaurs (half-human, half-horse), the most effective workers will seamlessly blend human and AI capabilities. Your platform should focus on creating these "centaur employees" in hotels—staff augmented by AI rather than replaced by it.
Embrace the Weird: AI behavior can be unpredictable and non-intuitive. Mollick argues successful adoption requires comfort with this uncertainty.
Final Thought:
"Here's my contrarian prediction: While everyone watches the next Sonder-style startup implode, the real winners of hospitality's AI revolution will be Booking.com, Expedia, and Airbnb. Why? They have what no startup can buy—billions in transaction data, millions of customer relationships, and the capital to deploy AI at scale. Airbnb is already moving into hotels, launching pilots in NYC, LA, and Madrid with independent properties, viewing it as a multibillion-dollar opportunity. Skift These platforms aren't just aggregators anymore—they're becoming AI-powered travel orchestrators that know more about guest preferences than any individual hotel or brand ever could. The brutal truth? In an AI-driven world, data is the new location, location, location. And the OTAs have been collecting it for decades while hotels fought over commission rates."
Cheers,
Sloan