Notion

Stripe

Notion

Notion uses freemium pricing. The free plan is generous — unlimited pages and blocks for individuals.

The Plus plan is $10/user/month for small teams. Business is $18/user/month.

Enterprise is custom-priced. The free tier is intentionally powerful enough that individuals and small teams can use it forever without paying.

The revenue comes when those individuals bring Notion to their companies and entire organizations adopt it.

Notion also has an AI add-on at $10/member/month that adds AI writing assistance, summarization, and Q&A across your workspace.

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.

Notion

Ivan Zhao studied cognitive science at the University of British Columbia, obsessed with the idea that computers should be creative tools, not just consumption devices. He was inspired by pioneers like Alan Kay and Douglas Engelbart who envisioned computers as tools for thought.

In 2013, he started Notion with the idea of building a tool that combined documents, databases, and project management into one flexible workspace.

The first version of Notion launched in 2015 and basically nobody cared. The product was too abstract.

People didn't understand what it was or why they needed it. The company burned through its initial funding.

By 2015, Notion was nearly dead — Zhao had to lay off almost the entire team.

With the last of his money, Zhao kept just one engineer — Simon Last — and moved to Kyoto, Japan, where the cost of living was a fraction of San Francisco. For over a year, Zhao and Last rebuilt Notion from scratch in a tiny apartment.

They rewrote the entire product, making it simpler and more intuitive. The 2.0 version launched in March 2018.

This time, it clicked. Product Hunt loved it.

Twitter loved it. Within months, Notion was growing 50% month over month.

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.

Notion

Notion grew almost entirely through organic love. The product was so flexible that users built incredible things with it and shared them on Twitter, YouTube, and Reddit.

Template creators built entire businesses around selling Notion templates. YouTubers made "my Notion setup" videos that got millions of views.

Notion didn't need a marketing team because its users were the marketing team.

The template ecosystem was a massive growth driver. Notion made it easy to duplicate and share templates.

Productivity influencers and creators built elaborate systems — life dashboards, second brains, CRM systems, content calendars — and shared them with their audiences. Every shared template was a free advertisement for Notion.

The community strategy was deliberate. Notion hired community managers early and empowered super-users to become Notion ambassadors.

There are Notion meetups in cities worldwide. Notion Campus Leaders run groups at universities.

The company understood that for a tool this flexible, community was the best way to teach people what's possible.

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 processing payments in 195 countries.

Notion

The "too flexible" problem. Notion can do almost anything, which means new users often stare at a blank page and have no idea where to start.

The learning curve isn't steep, but it's wide. People give up before discovering the product's power.

Every Notion user remembers the moment it finally "clicked" — but many potential users never reach that moment.

Enterprise adoption has been slower than expected. Notion is beloved by startups and small teams, but large enterprises need things like advanced permissions, audit logs, compliance certifications, and admin controls.

Building enterprise features while keeping the product simple for individuals is a constant tension. Companies like Confluence (Atlassian) have decades-long enterprise relationships that are hard to displace.

Performance at scale has been a persistent complaint. Notion pages with hundreds of blocks or large databases can become sluggish.

The app has improved significantly but power users with massive workspaces still hit performance walls. For a tool that promises to replace multiple apps, it needs to be as fast as each individual app it replaces.

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.

Notion

Notion is a workspace that combines notes, docs, wikis, project management, and databases into one tool. Pages can contain any mix of text, tables, kanban boards, calendars, galleries, and embedded content.

Notion Databases are the power feature — structured data that can be viewed as tables, boards, timelines, or calendars. Templates let users start with pre-built setups for everything from CRM to habit tracking.

Notion AI adds writing assistance, summarization, and the ability to ask questions about your workspace content. Notion Sites turns any Notion page into a published website.

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.

Notion

Index Ventures, Sequoia Capital, Coatue Management, Dragoneer Investment Group

Stripe

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