August Had 3 of the Year’s Biggest Startup Fundraises – Then a Slowdown

The first half of August saw three of the biggest travel startup fundraises of the year: Flyr ($295 million), Archer Aviation ($230 million), and Oyo ($173 million).

But overall, August was a slow month. Besides those three major raises, Skift identified fewer than 10 travel startups that raised money — all $10 million or less.

That includes only three announcements, highlighted below, over the past two weeks totaling $16.5 million.

That level of activity aligns with the funding trend that Skift has identified — more late-stage fundraises but fewer deals overall.

Uppercase: $9 Million

Uppercase, a luggage brand, has raised $9 million in series B funding from the venture capital firm Accel. 

That nearly doubles the startup’s valuation to $60 million. 

Mumbai-based Uppercase designs and sells roller suitcases, backpacks, and other types of travel gear.

Uppercase sells its products online and in 1,800 multi-brand stores across India. The company plans to open 10 exclusive retail stores throughout India by next month and expand to 50 stores in Europe and the Middle East by March 2025.

The company is targeting to more than double its revenue to $17.8 million by the end of this year.

Uppercase designs all of its products and works with Indian contract manufactureres. It’s planning to open its own manufacturing facility by December. 

Otto: $6 Million

Otto, an AI trip planner for business travel, has raised $6 million in seed funding. 

Madrona Ventures led the round, with support from Direct Travel and a star lineup of travel industry veterans. 

Steve Singh, managing partner for Madrona, led the investment from the firm and is the executive chairman of Otto. 

The angel investors include:

• Erik Blachford, former CEO of Expedia 
• Barney Harford, former CEO of Orbitz and board member of United Airlines
• Hugh Crean, former CEO of Farecast, a Madrona-backed airfare prediction company that was acquired by Microsoft in 2008

Seattle-based Otto is developing a virtual travel agent for planning and booking business trips, powered by the latest generative AI models. Much of the inventory is coming through a connection with ​​Spotnana. The founder and CEO is Michael Gulmann, a former senior vice president for Expedia.

(See Skift’s story.)

Betsy AI: $1.5 Million

Besty AI, a platform for automating short-term rental operations, has raised $1.5 million in seed funding. 

Leading investors for the round included Bungalow Capital, Ridge Ventures, and individual investor Ravi Belani. 

New York City-based Betsy AI provides clients with software for AI-powered guest messaging, upselling, review responses, and more. 

The startup works with more than 200 operators, including Host & Stay, Wynwood House, and Local Vacation Rentals.

Company	Stage	Lead	Raise
Uppercase	Series B	Accel	$9 million
Otto	Seed	Madrona Ventures	$6 million
Betsy AI	Seed	Bungalow Capital, Ridge Ventures	$1.5 million

Skift Cheat Sheet

Seed capital is money used to start a business, often led by angel investors and friends or family.

Series A financing is typically drawn from venture capitalists. The round aims to help a startup’s founders make sure that their product is something that customers truly want to buy.

Series B financing is mainly about venture capitalist firms helping a company grow faster. These fundraising rounds can assist in recruiting skilled workers and developing cost-effective marketing.

Series C financing is ordinarily about helping a company expand, such as through acquisitions. In addition to VCs, hedge funds, investment banks, and private equity firms often participate.

Series D, E, and, beyond These mainly mature businesses and the funding round may help a company prepare to go public or be acquired. A variety of types of private investors might participate.