Ramp

OpenAI

Ramp

Ramp makes money from interchange fees — the 1.5-2.5% that merchants pay on every credit card transaction. Unlike consumer cards that share interchange with users through rewards, Ramp gives a flat 1.5% cashback and keeps the rest.

The real business model is becoming the financial operating system for companies: once a company uses Ramp's card, they also use Ramp for expense management, bill pay, accounting automation, and procurement — all of which increase switching costs and customer lifetime value.

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.

Ramp

Eric Glyman and Karim Atiyeh had previously co-founded Paribus, a tool that automatically got refunds when prices dropped on things you'd already bought. Capital One acquired Paribus in 2016.

The experience taught them something: businesses were terrible at managing their spending, and the tools they used — corporate credit cards from Amex and Chase — were designed to encourage spending, not control it.

In 2019, they launched Ramp with a contrarian premise. Every other corporate card company made money by getting businesses to spend more (higher spend = more interchange revenue).

Ramp would make money from interchange too, but would actively help businesses spend less through automated expense management, duplicate subscription detection, and price negotiation.

The pitch to CFOs was irresistible: get a corporate card with 1.5% cashback, and we'll also find you an average of 5% savings on your total spending through our software. The card was the wedge.

The expense management platform was the real product.

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.

Ramp

Ramp grew by selling savings, not credit. The pitch to finance teams was: "We'll save you more money than we cost you." In an era when every company was looking to cut costs, Ramp offered a corporate card that came with a free expense management platform that actively found savings.

CFOs couldn't say no.

The product-led approach bypassed traditional enterprise sales cycles. A finance manager could sign up for Ramp, issue cards, and start seeing savings within a week — no six-month procurement process, no IT integration project.

The free expense management tools were so good that companies switched from Concur, Expensify, and Brex just for the software, with the card as a bonus.

Speed of execution was the differentiator. Ramp shipped features faster than any competitor.

They went from a corporate card to a full financial operations platform in three years. Every quarter, Ramp launched features that competitors took a year to build.

By 2024, over 25,000 businesses were using Ramp and the company was processing tens of billions in annualized spend.

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.

Ramp

Brex is the obvious competitor. Brex launched two years before Ramp with a similar corporate card concept and had the first-mover advantage.

But Brex pivoted away from small businesses to focus on enterprise in 2022 — angering thousands of existing customers — while Ramp doubled down on serving companies of all sizes. The competition has become a case study in strategic focus versus strategic pivots.

The "spend less" positioning has a mathematical ceiling. If Ramp's AI genuinely helps companies spend less, the interchange revenue from those companies also decreases.

There's an inherent tension between the mission (reduce spending) and the revenue model (earn a percentage of spending). Ramp has managed this by growing the customer base faster than individual customer spending declines.

Enterprise sales is the next frontier and it's expensive. Moving upmarket from startups and mid-market companies to Fortune 500 enterprises requires a sales team, implementation support, and enterprise features that cost real money to build and sell.

Ramp has been investing heavily in enterprise capabilities, but competing with Amex and JP Morgan for large corporate accounts is a different game than winning startups.

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.

Ramp

Ramp Corporate Card is the core — unlimited physical and virtual cards with 1.5% cashback and built-in spend controls. Ramp Expense Management automates receipt matching, policy enforcement, and reimbursements.

Ramp Bill Pay handles vendor payments and AP automation. Ramp Procurement manages vendor contracts and purchase approvals.

Ramp Intelligence uses AI to identify duplicate subscriptions, negotiate better rates, and flag wasteful spending. Ramp Flex offers flexible payment terms for businesses that need to extend their payables cycle.

Ramp Accounting automates close processes and syncs with QuickBooks, Xero, NetSuite, and Sage.

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.

Ramp

Founders Fund, D1 Capital, Stripe, Goldman Sachs, Thrive Capital, General Catalyst, Khosla Ventures

OpenAI

Microsoft ($13B), Thrive Capital, Khosla Ventures, Sequoia Capital, Founders Fund, Tiger Global, SoftBank, a16z