Stripe

Pinterest

Stripe

Stripe charges a flat 2.9% + $0.30 per transaction. That's it.

No setup fees, no monthly fees, no hidden charges. The simplicity is the product.

When a customer pays on a website using Stripe, Stripe handles everything — fraud detection, currency conversion, bank transfers, tax calculation, compliance. The merchant just sees money arrive in their account.

On top of the core payments, Stripe has built an entire financial infrastructure stack. Billing for subscriptions, Connect for marketplace payments, Atlas for incorporating a company, Issuing for creating virtual cards, Treasury for banking-as-a-service, and Radar for fraud prevention.

They're basically building the financial plumbing for the entire internet.

Pinterest

Pinterest makes money through advertising — specifically through "Promoted Pins" that look nearly identical to organic content. This is the magic of Pinterest's business model: ads don't interrupt the experience because the experience IS discovering products and ideas.

A promoted pin for a kitchen knife set appears right alongside organic pins of kitchen designs. The user doesn't distinguish between "ad" and "content" because both serve the same purpose.

Shopping ads are the fastest-growing segment. Brands upload their product catalogs, Pinterest matches products to user searches and boards, and users can buy directly through the platform or click through to the retailer's site.

Pinterest gets paid per click or per thousand impressions.

Revenue reached $3.65 billion in 2024, up from $3.05 billion the year before, and 2024 was its first genuinely profitable year. Average revenue per user is growing but still well below Meta's — the upside is enormous if Pinterest can close that gap.

Stripe

Patrick Collison was 19. His brother John was 17.

They had already built and sold a company — Auctomatic, an eBay auction tool — for $5 million while still teenagers in Limerick, Ireland. Patrick went to MIT, John went to Harvard, and they both dropped out because they had a better idea.

The idea was embarrassingly obvious in hindsight. In 2010, accepting payments on the internet was a nightmare.

You had to get a merchant account, negotiate with a payment processor, deal with a gateway provider, handle PCI compliance, and write thousands of lines of code. It took weeks or months.

The Collisons thought it should take five minutes.

They built a simple API — seven lines of code — that let any developer start accepting credit card payments immediately. No merchant account.

No paperwork. No phone calls with banks.

Just paste seven lines of code and you're in business. They originally called it /dev/payments, then changed it to Stripe in 2011.

Peter Thiel and Elon Musk — the PayPal mafia — were among the first investors. Sequoia and Andreessen Horowitz piled in soon after.

The Collisons had built exactly what every developer on Earth had been wishing for.

Pinterest

Ben Silbermann was a former Google ad operations employee who quit in 2008 to build apps. His first attempt was an iPhone app called Tote — essentially a mobile catalog that let women browse and bookmark products from fashion retailers.

Nobody downloaded it. But Silbermann noticed something in the data: users were saving products obsessively.

The collecting behavior was more interesting than the shopping behavior.

He teamed up with Paul Sciarra, a classmate from Yale, and Evan Sharp, a designer who was studying architecture at Columbia. Together they built Pinterest — a visual bookmarking tool that let people "pin" images from around the internet to organized boards.

Think of it as a digital mood board that anyone could make.

Pinterest launched as an invite-only beta in March 2010. Growth was painfully slow at first.

Silbermann personally wrote to the first 5,000 users, giving them his phone number and asking what they wanted. The early community was overwhelmingly women interested in home decor, fashion, recipes, and DIY projects.

By 2011, Time magazine named Pinterest one of the 50 best websites. By 2012, it was the fastest site in history to reach 10 million unique monthly visitors.

Stripe

Stripe grew almost entirely through developer love. They didn't hire a sales team for years.

They didn't run ads. They just built the best developer documentation anyone had ever seen and let word of mouth do the rest.

The developer-first strategy was deliberate. The Collisons realized that in a startup, the developer usually decides which payment provider to use.

If you make the developer happy, you win the company. Stripe's API documentation became legendary — clear, beautiful, with working code examples in every language.

They also grew by growing with their customers. Early Stripe customers included tiny startups that later became giants — Lyft, DoorDash, Instacart, Shopify.

As those companies scaled to billions in revenue, Stripe's processing volume scaled with them. Stripe didn't need to acquire new customers because its existing ones kept getting bigger.

The international expansion was methodical. Instead of launching everywhere at once like Uber, Stripe carefully added country after country, making sure each one worked perfectly with local payment methods, currencies, and regulations.

By 2024 they were letting businesses in dozens of countries take money from customers almost anywhere on earth, in 135 currencies.

Pinterest

Pinterest grew organically through women sharing boards with each other. The weddings use case was the killer app — brides-to-be would create boards for dresses, venues, flowers, and invitations, then share them with their wedding parties.

That viral loop drove millions of signups.

SEO is the secret weapon. Pinterest pages rank extremely well in Google Image Search.

Someone searching "modern living room ideas" often sees Pinterest results on page one. That drives a large stream of organic traffic from people who were not looking for Pinterest at all.

Unlike other social platforms, which compete with Google for attention, Pinterest quietly benefits from it.

The shopping pivot has been the growth unlock. Under CEO Bill Ready (former Google and PayPal executive who took over in 2022), Pinterest aggressively invested in shopping features — catalog integrations, buyable pins, merchant verification, and visual search for products.

The thesis: Pinterest users are already in a shopping mindset, so removing friction between "I like this" and "I bought this" is the straightforward path to revenue growth.

Stripe

Valuation whiplash. In 2021, Stripe hit a peak valuation of $95 billion during the fintech boom.

By 2023, they had to mark it down to $50 billion during the tech correction — a 47% drop that made headlines everywhere. Employees who had been paper millionaires suddenly weren't.

The valuation has since recovered to $91 billion after a secondary share sale in 2025, but those two years were rough for morale.

Competition is relentless. Adyen, the Dutch payments company, has been eating into Stripe's enterprise market.

Square (now Block) competes on the small business side. PayPal is everywhere.

New fintech players pop up constantly. The payments business has razor-thin margins and everyone is fighting for the same 2.9%.

Going public is the elephant in the room. Stripe has been expected to IPO for years.

Investors, employees, and the media keep asking when. The Collisons have consistently said they're in no rush, but with $8.7 billion raised and thousands of employees holding stock options, the pressure to provide liquidity is enormous.

As of 2025, they've opted for secondary sales instead of a public offering.

Pinterest

Pinterest's demographics are both an advantage and a limitation. The platform skews heavily female (over 60% women) and is strongest in home, fashion, food, and weddings.

Expanding beyond these categories to attract male users, younger demographics, and different use cases has been slow.

Competition for ad dollars is fierce. Pinterest competes with Meta, Google, TikTok, and Amazon for advertising budgets.

Most advertisers allocate the bulk of their spend to Meta and Google first, then consider others. Pinterest needs to prove its return on ad spend is competitive to win larger budget allocations.

Creator economy is underdeveloped. While Instagram, TikTok, and YouTube have massive creator ecosystems with monetization tools, Pinterest has historically been about content discovery, not content creation.

Users pin other people's content — the original creators often don't even know their work is on Pinterest. Building a creator program and driving original content creation on the platform has been a recent focus but lags far behind competitors.

Stripe

Stripe Payments is the core — accept credit cards, debit cards, Apple Pay, Google Pay, and 135+ payment methods in 195 countries. Stripe Connect lets marketplaces and platforms pay out to sellers (Shopify, Lyft, DoorDash all use it).

Stripe Billing handles subscription and recurring billing. Stripe Atlas lets you incorporate a US company from anywhere in the world — fill out a form, get a Delaware C-corp, bank account, and tax ID in days.

Stripe Radar uses machine learning to block fraud in real time. Stripe Treasury lets platforms offer banking services to their customers.

Stripe Tax automatically calculates and collects sales tax in every jurisdiction.

Pinterest

Pinterest Home Feed — the core discovery surface showing personalized pins based on user interests, boards, and search history. Pinterest Lens — visual search technology that lets users take a photo of any object and find similar items to buy on Pinterest.

Pinterest Shopping — integrated e-commerce allowing users to browse and purchase products directly from pins linked to retailer catalogs. Pinterest Boards — the organizing system where users save and categorize pins into collections, used for wedding planning, home renovation, recipes, fashion, and more.

Pinterest Shuffles — a collage-making app for Gen Z users to create aesthetic mood boards, driving younger user adoption.

Stripe

Peter Thiel, Elon Musk, Sequoia Capital, Andreessen Horowitz, General Catalyst, Founders Fund, Tiger Global, GV (Google Ventures), Goldman Sachs, Baillie Gifford

Pinterest

Bessemer Venture Partners, FirstMark Capital, and Andreessen Horowitz were early investors. Fidelity and Valiant Capital participated in later rounds.

Rakuten invested strategically. The April 2019 IPO raised $1.4 billion at a $12.7 billion valuation.

Elliott Management, the activist investor, took a large stake in 2022 and pushed for operational improvements that contributed to the company's path to profitability.