The $1.6t travel industry may be about to check out of its longtime hotels: Booking.com, Expedia, and Airbnb. The rise of AI agents that could book your next trip directly may be the biggest threat to OTAs yet.
Booking and Expedia have already inked deals with OpenAI to spin up AI trip planners, while Airbnb rolled out an AI-powered customer service bot and promised “agentic” features next year. But behind the optimism lies inherent paranoia: if autonomous agents can comb hotel and airline sites directly, these platforms’ lucrative 15–20% commissions could vanish.
Hoteliers, long resentful of those fees, smell opportunity. “Fundamentally, [OTAs] are parasitic,” one investor argued, suggesting hotels could use the freed-up margins to sweeten customer perks. Meanwhile, fintech is circling: the same shift that threatens OTAs could accelerate the use of virtual cards in travel booking. For hotels and airlines, virtual cards promise better payment control, fraud reduction, and lower costs, and these advantages could compound if AI agents start transacting at scale without platform middlemen.
Today, OTAs still wield massive advantages: unrivaled datasets, traveler loyalty, and infrastructure that Big Tech might struggle to replicate. But as Glenn Fogel of Booking admitted, there’s “no such thing as a moat” in an AI-first world. If agents truly learn how to plan travel seamlessly, the biggest trip OTAs might be booking is their own exit.

Portfolio News
Flutterwave Partners with Clear Junction to enhance cross-border payments - Flutterwave now has access to Clear Junction’s robust technical infrastructure and faster transaction routing. This marks a significant milestone in addressing the evolving needs of migrant workers and families relying on dependable cross-border money flows. Flutterwave taps into Clear Junction’s expertise in facilitating cross-border trade payment and treasury services to enhance its support for African remittance customers making cross border payments to the UK and EU. Read more
Agents of Change
Online travel platforms prepare for rise of artificial intelligence ‘agents’ - The moves come as makers of AI agents develop technology designed to make travel arrangements for users based on their unique preferences. This could upend the $1.6t global travel market, allowing more hotels and airlines to be accessed directly, and would disrupt the business model of dominant online travel agents that rely on the commissions and fees they can charge those businesses. Read more
Industry News
Klarna’s stock jumps 15% in NYSE debut after pricing IPO above range - Klarna priced shares at $40 on Tuesday, raising $1.37b for the company and existing shareholders. The IPO marks the latest in a growing list of high-profile tech listings this year, suggesting increased demand from Wall Street for new offerings. Companies like stablecoin issuer Circle and design software platform Figma soared in their respective debuts. Meanwhile, crypto exchange Gemini is expected to go public later this week. Read more
Robinhood aims social platform at Reddit’s WallStreetBets - Robinhood is breaking into social media with a platform called Robinhood Social, where retail traders can share their positions and post about their investment victories. Robinhood Social will also allow investors to follow the moves and statistics of other users, including their profit and loss statements and profit rates, and will include profiles for public figures with their trades populated via public disclosures. Read more
Wall Street courts retail traders to supercharge IPOs - Retail traders, long considered dumb money by Wall Street, have changed investment dynamics in everything from individual stocks to crypto to one-day options. Now they’re throwing their weight around in the IPO market — and companies are welcoming them with open arms. Read more
Nasdaq seeks rule change with SEC to trade tokenized stocks - The exchange operator is seeking approval from the US Securities and Exchange Commission to amend certain rules, including the definition of a security, that would allow stocks to be tokenized and traded on regulated venues like Nasdaq, according to a filing Monday. Any changes would have to be approved by the SEC and need to go through a comment period before implementation. Read more
Robinhood captures a spot on S&P 500 - Robinhood Markets has replaced Caesars Entertainment on the S&P 500, with S&P Dow Jones Indices announcing that change will go into effect Sept. 22. Joining Robinhood among new inductees is the marketing platform AppLovin, replacing bond trading platform MarketAxess, and electrical construction services provider Emcor, replacing the solar inverter company Enphase Energy. Read more
The hot investment with a 3,000% return? Pokémon cards - Pokémon cards, which pay no dividends and aren’t subject to financial regulation, have seen a roughly 3,821% monthly cumulative return since 2004, according to an index by analytics firm Card Ladder tracking trading-card values through August. That trounces the S&P 500’s 483% jump over the same period. Read more
Figure CEO sees IPO as a catalyst for its next phase - Figure views its upsized IPO as "fuel to expand and to be a first mover," CEO Michael Tannenbaum says. The blockchain lender is betting investors will treat it less like a consumer lender and more like an exchange operator. Its shares opened today at $36, or over 40% above its $25 IPO price, giving the company a market value of around $7.6b. Read more
Mistral is stirring up a storm in European tech - The €1.3b investment this week by Dutch tech company ASML in the French AI start-up Mistral brings the backing of a manufacturer of highly complex industrial equipment, known for its $400m extreme ultraviolet lithography machines used to make state-of-the-art semiconductors. Read more
Robots step in more than ever when credit traders go on vacation - Algorithmic trading accounted for more than 40% of trading in the US high-grade market in August, a percentage that has climbed steadily since 2020. Algorithms are pushing the frontier — broadening coverage, smoothing liquidity and sustaining market presence through both turbulent and traditionally slower periods. Read more
Select Financings
Accordance - San Francisco based AI powered platform for accounting and tax firms raised $10m in Seed funding led by Khosla Ventures. Read more
Cassidy - New York City based AI automation platform for non technical teams raised $10m in Series A funding led by HOF Capital. Read more
Clockwork - San Francisco based AI compute company raised $20.6m in new funding led by New Enterprise Associates. Read more
Hush Security - Tel Aviv Israel based machine access security company raised $11m in Seed funding led by Battery Ventures. Read more
Kamino - São Paulo based financial operating system raised $10m in Series A funding led by Flourish Ventures. Read more
Kin - Chicago based homeowners insurance company raised $50m in Series E funding led by QED Investors. Read more
Klaar - San Francisco based AI powered performance management platform raised $5m in Series A funding led by Prime Venture Partners. Read more
Koi - Washington DC based software security platform raised $48m in seed funding led by Battery Ventures. Read more
Rainforest - Atlanta based payments company raised $29m in Series B funding led by Matrix Partners. Read more
Standard Fleet - San Francisco based fleet management platform raised $13m in Series A funding led by Nova Threshold. Read more
Ume - São Paulo based infrastructure developer for credit businesses raised $22m in Series B funding led by Valor Capital Group. Read more
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