Robinhood

OpenAI

Robinhood

Robinhood makes money in ways that don't involve charging users directly. The biggest revenue source is payment for order flow (PFOF) — when users place a trade, Robinhood routes it to market makers like Citadel Securities, who pay Robinhood for the right to execute the trade.

This generates hundreds of millions annually. Robinhood also earns interest on uninvested cash sitting in user accounts, margin lending (charging interest when users borrow money to trade), and Robinhood Gold — a $5/month subscription for larger instant deposits, professional research, and higher interest on cash.

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.

Robinhood

Vlad Tenev and Baiju Bhatt met as physics and math students at Stanford. After graduating, they moved to New York and started two fintech companies that sold trading software to hedge funds.

While building tools for Wall Street, they noticed something absurd: it cost brokerages essentially nothing to execute a trade electronically, but they were charging retail investors $7-10 per trade.

The math was simple. Electronic trading had driven costs to near zero, but brokerages kept the old pricing because customers didn't know better.

Tenev and Bhatt thought: what if we just charged zero? In 2013, they founded Robinhood with the explicit mission of democratizing finance — giving everyone access to the stock market with no commissions, no minimums, and a beautiful mobile app.

The app launched in 2014 with a waitlist that hit 1 million people before the product was even available. The pink-and-green design, the confetti animation when you made a trade, and the simplicity of the interface made investing feel approachable.

For millions of young Americans who had never bought a stock, Robinhood was the entry point.

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.

Robinhood

Robinhood grew by making investing feel like a game. The app was designed to be addictive — swipe to trade, confetti for your first purchase, notifications about stock movements.

It was investing designed for the smartphone generation. Critics called it "gamification of finance." Users called it the first trading app that didn't feel like it was designed in 1997.

The referral program was massive. Both the referer and the new user got a free stock when someone signed up.

People were getting free shares of Apple or Ford just for downloading the app. It spread through college campuses like wildfire.

By 2020, the average Robinhood user was 31 years old — decades younger than the average brokerage customer.

Zero commissions forced the entire industry to follow. In October 2019, Charles Schwab, TD Ameritrade, E-Trade, and Fidelity all dropped their trading commissions to zero within days of each other.

Robinhood had single-handedly destroyed the commission-based brokerage model that had existed for decades.

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.

Robinhood

GameStop was the worst week in Robinhood's history. In January 2021, Reddit's r/WallStreetBets community drove GameStop stock from $20 to $483.

Millions of Robinhood users were buying. Then on January 28, Robinhood restricted buying of GameStop and several other meme stocks.

Users could only sell, not buy. The stock crashed.

The backlash was nuclear. Users accused Robinhood of siding with hedge funds against retail investors.

Vlad Tenev was dragged before Congress. The real reason was less sinister but equally damaging — Robinhood's clearinghouse (DTCC) demanded $3 billion in additional collateral due to the extreme volatility, and Robinhood didn't have it.

They had to raise $3.4 billion in emergency funding over a weekend. The company that built its brand on democratizing finance had restricted the most democratic stock trade in history.

The payment for order flow controversy never goes away. Critics argue that PFOF creates a conflict of interest — Robinhood profits by routing user trades to market makers rather than getting users the best possible price.

The SEC has considered banning PFOF entirely. If that happens, Robinhood loses its largest revenue source.

Post-IPO performance was brutal. Robinhood went public in July 2021 at $38 per share.

The stock briefly hit $70 on meme stock momentum, then cratered to under $8 by mid-2022 — a 90% decline. The company laid off 9% of staff in April 2022 and another 23% that August.

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.

Robinhood

Robinhood is a stock, options, and crypto trading app. The core product lets you buy and sell stocks, ETFs, and options with zero commissions.

Robinhood Crypto adds trading for Bitcoin, Ethereum, and other cryptocurrencies. Robinhood Gold is the premium tier — higher interest on cash, larger instant deposits, and Morningstar research reports.

Robinhood Cash Card is a debit card that earns cashback and rounds up purchases to invest spare change. Robinhood Retirement offers IRA accounts with a 1% match on contributions.

Robinhood Legend is their new desktop trading platform aimed at active traders.

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.

Robinhood

Sequoia Capital, Ribbit Capital, NEA, Index Ventures, Andreessen Horowitz, DST Global, D1 Capital

OpenAI

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