Compare / OpenAI vs Skyscanner
AT A GLANCE
FUNDING HISTORY
OpenAI
Skyscanner
BUSINESS MODEL
OpenAI
OpenAI makes money primarily through API access and subscriptions. The API charges developers per token (roughly per word) for using GPT models in their applications.
ChatGPT Plus costs $20/month for individual users, ChatGPT Team is $25-30/user/month, and ChatGPT Enterprise is custom-priced. Microsoft pays OpenAI licensing fees and also resells OpenAI models through Azure OpenAI Service.
OpenAI's annualised revenue ran past $13 billion during 2025 and kept climbing from there, which is the kind of growth curve that normally only exists in a pitch deck.
Skyscanner
Meta-search model. Skyscanner doesn’t sell tickets directly — it redirects users to airlines or OTAs (Online Travel Agencies) and earns a commission on each click-through or completed booking.
This asset-light model means Skyscanner doesn’t hold inventory or handle customer service for bookings.
Revenue also comes from advertising and sponsored placements within search results.
HOW THEY STARTED
OpenAI
OpenAI was founded in December 2015 as a nonprofit AI research lab. The founding donors — including Elon Musk, Sam Altman, Peter Thiel, Reid Hoffman, and Jessica Livingston — pledged $1 billion with a mission to build artificial general intelligence (AGI) that would benefit all of humanity.
The idea was that AI was too important and too dangerous to leave in the hands of Google alone.
Sam Altman became chairman while Greg Brockman (former CTO of Stripe) became president. Ilya Sutskever, one of the most respected AI researchers alive, left Google Brain to become chief scientist.
The early team was stacked with world-class researchers who published their work openly — hence "Open" AI.
But AI research turned out to be staggeringly expensive. Training large models required millions of dollars in compute.
In 2019, OpenAI created a "capped-profit" subsidiary — investors could earn up to 100x their money, but profits beyond that would flow to the nonprofit. Microsoft invested $1 billion.
The mission was still to save humanity. The method now involved making a lot of money first.
Skyscanner
Gareth Williams was a programmer in Edinburgh who wanted to find cheap flights to go skiing. In 2003, the only way to compare flight prices was to check each airline’s website individually.
Google Flights didn’t exist. Online travel agencies had limited inventory.
Williams, Barry Smith, and Bonamy Grimes built Skyscanner as a flight price comparison engine that searched across airlines and travel agents to show all options on one page. It launched in 2003 and grew through word of mouth among budget-conscious travelers.
HOW THEY GREW
OpenAI
ChatGPT's launch in November 2022 was the growth strategy — it just wasn't planned that way. The team expected a modest research preview.
Instead, ChatGPT hit 1 million users in 5 days and 100 million monthly active users in 2 months, making it the fastest-growing consumer application in history. The product went viral because it felt like magic — for the first time, anyone could have a natural conversation with a machine that seemed to understand them.
The Microsoft partnership provided distribution at massive scale. Microsoft integrated OpenAI models into Bing, Office 365 (Copilot), GitHub (Copilot), and Azure.
Overnight, hundreds of millions of Microsoft users had access to OpenAI technology. Microsoft's $13 billion investment was the largest AI bet in history and gave OpenAI nearly unlimited compute.
The API created an ecosystem. Thousands of startups built products on top of OpenAI's models — from customer service bots to coding assistants to content generators.
Each API customer locked themselves into OpenAI's ecosystem, creating switching costs and recurring revenue.
Skyscanner
SEO domination for flight search queries. In many European and Asian markets, Skyscanner ranks #1 for "cheap flights" and similar terms.
The site was translated into 30+ languages and optimized for each market. Mobile app downloads added hundreds of millions of users.
THE HARD PART
OpenAI
The board crisis of November 2023 nearly destroyed the company. The nonprofit board fired Sam Altman as CEO on a Friday, citing a loss of confidence.
Within 48 hours, 95% of employees threatened to quit and follow Altman to Microsoft. By Tuesday, Altman was reinstated and the board was restructured.
The incident exposed the fundamental tension between OpenAI's nonprofit governance and its for-profit ambitions — a tension it finally addressed in late 2025 by restructuring the business as a public benefit corporation sitting under the original nonprofit.
The cost of training frontier models is eye-watering. Each new GPT generation costs hundreds of millions to train.
OpenAI is reportedly spending over $7 billion annually on compute. The company is burning through cash faster than almost any startup in history, which is why it keeps raising at higher and higher valuations.
If revenue growth slows before costs stabilize, the math gets ugly.
Safety concerns are not going away. Multiple prominent researchers have left OpenAI over disagreements about the pace of development versus safety research.
Ilya Sutskever, the chief scientist who was central to the board's decision to fire Altman, left in 2024 to start a safety-focused AI lab. The public debate about whether OpenAI is moving too fast — and whether its safety commitments are genuine — grows louder with every capability improvement.
Skyscanner
Google Flights is a massive existential threat — Google can surface flight prices directly in search results before users even reach Skyscanner. The meta-search model depends on airlines and OTAs being willing to pay for clicks, which they can negotiate down as they gain direct booking capabilities.
THE PRODUCTS
OpenAI
ChatGPT is the consumer chatbot — the product that made AI mainstream overnight. The flagship GPT models are multimodal, handling text, images, and audio in one system.
The OpenAI API lets developers integrate GPT into any application. DALL-E generates images from text descriptions.
Whisper transcribes and translates audio. Sora generates videos from text prompts.
GPT Store lets users create and share custom GPT agents. ChatGPT Enterprise gives businesses a private, secure version of ChatGPT with admin controls and no data training.
Skyscanner
Flight search and comparison across thousands of routes. Hotel comparison.
Car rental comparison. "Everywhere" search — discover the cheapest destinations from your airport.
Price alerts for specific routes. Flexible date search.
WHO BACKED THEM
OpenAI
Microsoft ($13B), Thrive Capital, Khosla Ventures, Sequoia Capital, Founders Fund, Tiger Global, SoftBank, a16z
Skyscanner
Sequoia Capital led the $192 million investment in 2016. Scottish Enterprise supported early development.
Trip.com Group (formerly Ctrip) acquired Skyscanner for $1.74 billion in 2016.