DoorDash

OpenAI

DoorDash

DoorDash operates a three-sided marketplace connecting restaurants, delivery drivers (Dashers), and consumers. Revenue comes from three streams: commissions charged to restaurants (typically 15-30% of the order value), delivery fees and service fees charged to consumers, and DashPass subscription revenue ($9.99/month for free delivery and reduced fees).

The DashPass subscription is the retention engine. Over 18 million subscribers pay monthly whether they order or not, creating predictable recurring revenue.

Subscribers order more frequently (about 4x more than non-subscribers), increasing order volume.

Advertising is the emerging high-margin business. Restaurants pay for promoted listings and sponsored placements in the app.

This is essentially a search advertising business built on top of a logistics network. Ad revenue has grown to over $1 billion annually — and it's nearly pure profit because it costs almost nothing to display an ad.

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.

DoorDash

Tony Xu grew up watching his mother work multiple restaurant jobs after the family immigrated from Nanjing, China to Illinois. She washed dishes, waited tables, and cooked — sometimes all in the same week at different restaurants.

That experience gave Xu an unusual understanding of how brutally hard the restaurant business is.

At Stanford in 2012, Xu and classmates Stanley Tang, Andy Fang, and Evan Moore were in a startup class looking for a business idea. They interviewed over 200 small business owners and kept hearing the same problem: restaurants wanted to offer delivery but couldn't afford to hire drivers.

Domino's and Pizza Hut had fleets. Your local Thai place didn't.

Their solution was comically low-tech. They built a one-page website called PaloAltoDelivery.com, listed menus from local restaurants (without asking permission), and put their personal phone numbers on the site.

When orders came in, they drove the food themselves. The first order was pad thai from a restaurant in Palo Alto.

Within months, they were drowning in orders and realized this was a massive business. They incorporated as DoorDash in January 2013 and got into Y Combinator that summer.

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.

DoorDash

DoorDash won the US market through obsessive focus on suburban and mid-market restaurants — the segments Uber Eats and Grubhub ignored. While competitors fought over Manhattan and San Francisco, DoorDash was onboarding every Chinese restaurant and pizza shop in Tucson and Des Moines.

By the time competitors noticed, DoorDash had locked up the majority of US restaurants.

The "last-mile logistics" expansion is the long game. DoorDash now delivers groceries (partnerships with Albertsons, Rite Aid), convenience items (DashMart dark stores), alcohol, pet supplies, and retail products.

The thesis is that once you have a network of drivers and a consumer habit of ordering through an app, you can deliver anything — not just food.

The Wolt acquisition for $8.1 billion in 2022 was the international play. Instead of grinding through country-by-country expansion, DoorDash bought the leading delivery platform in 23 countries across Europe and Asia.

Wolt brought strong unit economics and a beloved brand, especially in the Nordics.

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.

DoorDash

Profitability has been the constant question. DoorDash lost money every year through its IPO and beyond, finally posting its first full year of profit in 2024.

The food delivery business has razor-thin margins — restaurants want lower commissions, drivers want higher pay, and consumers want lower prices. Squeezing profit from that three-way tension is incredibly hard.

Regulatory risk is real and growing. Cities and states have capped delivery commissions (New York City caps at 15% for delivery, 5% for marketing).

Worker classification lawsuits keep coming — are Dashers employees or independent contractors? California's Prop 22 temporarily settled this for California, but the debate rages everywhere else.

Each new regulation shaves margin.

Uber Eats is the forever competitor. Uber's massive ride-sharing network gives them built-in driver supply and brand recognition.

They're willing to lose money on Eats to keep their broader ecosystem sticky. DoorDash and Uber Eats together control about 90% of US delivery, and neither can afford to cede ground.

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.

DoorDash

DoorDash Marketplace — the core food delivery platform connecting consumers to 390,000+ restaurant partners across the US, Canada, Australia, Japan, and Germany. DashPass — a subscription program offering $0 delivery fees and reduced service fees for $9.99/month.

The loyalty engine of the entire business. DoorDash Drive — a white-label delivery service that lets any business (not just restaurants) use DoorDash's driver network to fulfill their own orders.

Basically DoorDash as a logistics API. DoorDash for Business — a corporate platform for team meals, employee benefits, and office food programs.

Wolt — the European food delivery platform DoorDash acquired for $8.1 billion in 2022, now the company's international expansion vehicle.

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.

DoorDash

Sequoia Capital has been the most consequential investor, leading multiple rounds and backing Tony Xu from Y Combinator onward. Khosla Ventures, Kleiner Perkins, and SoftBank Vision Fund participated in growth rounds.

Y Combinator was the starting point (Summer 2013 batch). The December 2020 IPO raised $3.4 billion at a $39 billion valuation, making it one of the biggest tech IPOs of that year.

OpenAI

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