Travel Tech Essentialist #193: Direction

Where things are going matters more than how fast they're moving. This edition looks at where leverage is showing up, how founders are finding product-market fit with AI, and why trust is the missing layer for agents. There's also a quiet shift back toward in-person connection, both at work and in life.

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1. Why agents aren’t booking travel yet

This post from Theory VC looks at why AI agents still struggle with real-world tasks like buying a car or booking international flights. The issue isn’t tools or intelligence. It’s trust. Most decisions fall outside a user’s “zone of comfort,” where the perceived consequences are too high or reversibility is too low. Booking travel, especially across systems and currencies, is still seen as a one-way door decision. There’s no good way to undo a bad booking, so users (and agents) hesitate. In contrast, software development works well for agents because it’s full of systems that make decisions easy to reverse and consequences easier to manage. Until those support systems for travel and other domains exist, agents will be limited to safer, more controlled environments.

2. AI prompts to find cheap flights

An X thread by Gina Acosta, viewed over 4.6 million times and bookmarked 63,000 times, shares six prompts she used in Grok to uncover flight-pricing tricks. One of them surfaced a $340 fare on a route that usually costs $1,200.

One of them: "Explain hidden city ticketing for my route from [departure] to [destination]. Find flights where [destination] is a layover city on a longer route that costs less. What are the risks, rules, and how much could I save? Give me specific flight examples."

3. What early AI success looks like

Bessemer Venture Partner’s State of AI report is a monster and well worth a read. It tries to make sense of the post–ChatGPT landscape with real benchmarks and clear patterns for what early success looks like. The report doesn’t just describe patterns; it backs them up with detailed examples of real startups.

They analyze two winning AI startup archetypes:

• “Supernovas” grow fast, hitting ~$40M ARR in year one and ~$125M in year two, but often with lower (average 25%) or negative margins and ~$1.13M ARR per FTE.

• “Shooting Stars” look more like great SaaS companies: ~$3M ARR in year one, 4x YoY growth, 60% gross margins, and ~$164K ARR per FTE in their first years

Bessemer’s point is that this era won’t be defined by a few outlier Supernovas, but by hundreds of Shooting Stars. That’s the benchmark most founders should focus on.

The report also looks into fast-moving areas such as vertical AI, agent-native browsers, and memory as a product feature. It looks at how AI is changing not just what software does, but how it works…tools that don’t just store data but act on it. It’s not travel-specific, but if you’re building in or around AI, there’s a lot in here that applies.

4. What gives AI founders an edge right now

Bessemer’s report is also about why some teams get there and others don’t. The difference is founders who understand what AI is genuinely good at, where it breaks down, and how to design around both. Products that remember, adapt, and plug into real workflows are proving harder to replace.

A few of their takeaways:

• Start with an AI wedge: Solve a narrow, high-friction problem (e.g., legal research, sales notes). Deliver 10x value fast, then expand.

• The browser is your canvas: Agentic AI is shifting to the browser layer; now a programmable environment where agents observe and execute. Build for this surface; it’s the new operating layer.

• Vertical AI is the new SaaS: “Technophobic” industries are adopting AI fast. Win by embedding deeply, proving ROI from day one, and scaling quickly.

• Incumbents are awake and acquisitive: SaaS giants are buying their way into AI. Build technical and data moats. Be M&A-ready, but operate like you’ll own the category.

• Taste and judgment are your differentiators: In a world of agents and automation, human insight is the edge. Founders who intuit what should exist (not just what can) will define the next era.

5. $1B plan to make airports more “family-friendly”

The U.S. Department of Transportation is investing $1 billion to improve the airport experience, with a focus on families. Plans include kids’ play areas, nursing pods, yoga rooms, and healthier food options. The initiative follows a recent DOT call for more civility and “elegant attire” in air travel. Some airport architects point out that many of these upgrades are already underway, while others question whether amenities like gyms or kale will move the needle. Critics say the focus should be on basics: clearer announcements, working infrastructure, and less crowding. Read + AFAR

6. How travel companies score on culture

The Economist partnered with CultureX, a firm co-founded by MIT Sloan’s Donald Sull, to analyze employee reviews from 900 companies across 19 industries, including Travel & Leisure. Using language models to assess how employees describe their experience (not just ratings), they scored companies on topics like leadership, work-life balance, transparency and agility. The interactive tool lets you explore how companies compare and how their cultures have shifted post-COVID. Read +

7. The quiet return to office

Return-to-office pressure is picking up again, but more through signals than mandates. Promotions tied to face time, tighter tracking, and the quiet understanding that being in the room still matters. The WSJ calls it “hybrid creep,” and the data backs it up: office buildings tracked by JLL are now 67% full on Mondays and 56% full on Fridays. Mondays are now as busy as Wednesdays were in 2023. Fridays have almost caught up to Wednesday levels from 2022.

Culture is shaped more by what gets rewarded than what’s written down. Shout out to my friend Dave Morgan, founder and CEO of Simulmedia, who doesn’t play games with this stuff: “If companies believe that their teams are better together, in person in office, they should be open & explicit about it. That’s what Simulmedia does. No stealth. No games.”

8. Where the leverage is

In 2025, Alphabet’s market cap rose from $2.3 trillion to $3.8 trillion, adding $1.5 trillion in value in a single year. That’s more than five times the combined market caps of Booking (~$175B), Airbnb (~$84B), and Expedia (~$34B). Put differently, Google created more value in one year than three decades of the world’s largest online travel agencies.

Of course, it’s an apples-to-oranges comparison…search, ads, and infrastructure operate on a very different scale than travel transactions. But that’s the point. The deeper you are in the intent layer, the more everything compounds.

9. Brand quakes: details that redefine loyalty

Rory Sutherland’s “brand quake” is the moment a brand does something so unexpectedly good that it permanently upgrades how a customer feels about it. It is less about being good on average and more about a vivid, emotional peak that rewires loyalty and drives word of mouth. He often illustrates this with the post office: if your postman is unexpectedly kind, reliable, and genuinely helpful, that interaction overwhelms whatever the official marketing says about the postal service. And vice versa, of course. The everyday human contact becomes the brand, because that is what people actually feel and remember.

In travel, disruption moments (delays, cancellations, failed bookings, medical or logistical scares, etc…) are prime quake territory. Most brands respond with rigid policies, but a brand-quake mindset asks: how can this be turned into a story the traveler can’t stop retelling? Proactive rebooking, generous credits, or a human follow-up can create a quake that makes price and feature comparisons less relevant and turns a functional platform into a trusted companion. Faye Insurance is a good example of a company that appears to understand this, operating as if its main job is to turn stressful, high-stakes situations into reassuring, story-worthy experiences rather than bureaucratic nightmares.

10. The offline experience is a growth bet

In the past month, over $500M in funding has gone to companies betting on in-person connection. Andreessen Horowitz launched an invite-only dinner series for founders. Rodeo, started by Hinge’s former COO, is building tools to help people spend more time with friends offline. The former Hinge CEO is working on Overtone, an AI-powered dating app focused on IRL outcomes. Ari Emanuel, CEO of TKO, just launched MARI, a new global live events company. Startups are also hiring for roles focused entirely on real-world engagement.

There’s clear momentum behind products that bring people together face-to-face. Travel has always been about in-person connection. The opportunity now is building tools that make those moments easier to access, share, and return to. (Via The Collective)

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Mauricio Prieto