Warby Parker

OpenAI

Warby Parker

Vertically integrated DTC eyewear — Warby Parker designs frames in-house, contracts manufacturing directly (cutting out the brand licensing middlemen), and sells directly to consumers through its website and owned retail stores. The $95 price point (later raised to $95-$195) eliminates the traditional retail markup chain.

Home Try-On program lets customers pick five frames to try for free before buying. Revenue comes from prescription glasses, sunglasses, contact lenses, and eye exams (offered in stores).

The company expanded from pure e-commerce into physical retail with 200+ stores, making it an omnichannel brand rather than purely online.

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.

Warby Parker

Neil Blumenthal lost a pair of glasses backpacking and couldn't believe replacing them cost $700. He mentioned this at Wharton Business School, where classmates Dave Gilboa, Andrew Hunt, and Jeffrey Raider were having the same reaction.

They dug into the economics and discovered that Luxottica — an Italian conglomerate most people have never heard of — owned Ray-Ban, Oakley, LensCrafters, Sunglass Hut, Pearle Vision, and the licensing rights for Chanel, Prada, and Versace. One company controlled the supply chain from design to retail and priced accordingly.

The four students launched Warby Parker in February 2010 with a simple website selling prescription glasses for $95 — about a quarter of what Luxottica charged. GQ called them "the Netflix of eyewear" before they'd shipped their 100th pair.

They hit their first-year sales target in three weeks and had a 20,000-person waitlist within 48 hours of launch.

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.

Warby Parker

The DTC playbook: build a beautiful brand, price dramatically below incumbents, and tell a compelling story about why the old way was a rip-off. The Home Try-On program was brilliant viral marketing — people posted photos of themselves in five different frames on social media asking friends to vote.

"Buy a Pair, Give a Pair" philanthropy (one pair donated for every pair sold) gave the brand a social mission that resonated with millennials. Physical retail expansion gave customers who wanted to try before they buy a real store experience.

Celebrity endorsements and fashion magazine coverage positioned Warby Parker as a lifestyle brand, not just a discount option. Steady geographic expansion of stores into new markets, each store becoming a customer acquisition channel.

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.

Warby Parker

Luxottica (now EssilorLuxottica after merging with the world's largest lens maker) remains a $90 billion behemoth with resources Warby Parker can't match. Post-IPO stock performance has been disappointing — shares fell over 70% from their 2021 highs as the DTC bubble deflated.

Physical retail expansion is capital-intensive and each store needs to reach profitability. Competition from dozens of DTC eyewear brands (Zenni, EyeBuyDirect, Pair Eyewear) that copied the model and often undercut Warby Parker on price.

Prescription eyewear requires optometrist involvement, which adds complexity and regulatory overhead compared to selling non-prescription consumer products. And the fundamental challenge of glasses: people only buy them every 1-3 years, making customer lifetime value dependent on retention across very long purchase cycles.

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.

Warby Parker

Prescription eyeglasses starting at $95 including basic lenses — the product that broke the Luxottica pricing model. Home Try-On — pick five frames online, receive them in a box, try them at home for free, return what you don't want.

Progressive lenses and blue-light-filtering options for higher-end needs. Prescription and non-prescription sunglasses.

Scout contact lenses — Warby Parker's daily disposable contact lens brand. In-store eye exams with licensed optometrists.

Virtual Try-On using iPhone face-scanning technology to see frames on your face through the app.

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.

Warby Parker

Pre-IPO investors included General Catalyst, Tiger Global Management, T. Rowe Price, Durable Capital Partners, and D1 Capital Partners.

The company went public on the NYSE in September 2021 via direct listing.

OpenAI

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