Robinhood

Zoom

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.

Zoom

Zoom uses a freemium model. Free accounts get unlimited one-on-one meetings and 40-minute group meetings.

Paid plans start at $13.33/month per user for Pro (meetings up to 30 hours), $18.33/month for Business, and custom pricing for Enterprise. Zoom also charges for add-ons — Zoom Phone (cloud phone system), Zoom Rooms (conference room hardware), and Zoom Contact Center.

The free tier is the hook. The 40-minute limit on group calls creates just enough friction to push power users to pay.

And once one person in a company pays, the whole team follows because nobody wants to be the one whose meetings keep getting cut off.

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.

Zoom

Eric Yuan grew up in Tai'an, a mining city in Shandong province, China. In the mid-1990s he was in his twenties and inspired by the internet boom happening in America.

He applied for a US visa. He was rejected.

He applied again. Rejected again.

Eight times in total over about two years before he was finally approved in 1997. He moved to Silicon Valley with barely any English and joined WebEx as one of its first engineers.

Yuan spent 14 years at WebEx, eventually becoming VP of Engineering. Cisco acquired WebEx in 2007 for $3.2 billion.

Yuan watched Cisco slowly bloat the product with enterprise features while the core video quality deteriorated. He kept telling Cisco leadership they needed to rebuild the product from scratch.

They kept saying no.

In 2011, Yuan quit and took 40 WebEx engineers with him. He founded Zoom Video Communications with a simple thesis: video meetings should just work.

No downloads. No lag.

No "can you hear me?" No IT department required. He built the product that Cisco refused to build.

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.

Zoom

Zoom grew on one thing: it worked. In a world where every video call started with five minutes of technical issues, Zoom calls just connected.

That reliability was the entire marketing strategy for the first five years.

The freemium model did the rest. Teachers, coaches, therapists, book clubs, and small teams all started on the free tier.

When they hit the 40-minute limit, enough of them converted to paid. And every free meeting was essentially a demo — everyone in the meeting saw how good Zoom was.

Yuan obsessed over simplicity. While competitors like WebEx and GoToMeeting required downloads, plugins, and IT involvement, Zoom worked in the browser with one click.

The learning curve was essentially zero. Your grandmother could figure it out.

That turned out to be extremely important when a pandemic suddenly required your grandmother to figure it out.

Then COVID happened. In March 2020, the world shut down.

Every meeting — work, school, family, doctor, church, happy hour — moved to video. Zoom was already the easiest option.

Daily participants exploded from 10 million to 300 million in four months. The stock went from $70 to $588.

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.

Zoom

The post-pandemic hangover has been severe. Zoom's stock peaked at $588 in October 2020 and crashed to under $70 by 2022 — an 88% drop.

The company went from the most exciting tech stock on the planet to a cautionary tale about pandemic valuations. Revenue growth slowed from 300%+ to single digits as people returned to offices and competitors caught up.

Security and "Zoombombing" were early crises. In early 2020, as millions of new users flooded in, trolls discovered they could join open Zoom meetings and share offensive content.

Schools, churches, and AA meetings were disrupted. It turned out Zoom's encryption wasn't truly end-to-end as advertised.

Yuan had to halt all feature development for 90 days and focus exclusively on security fixes. It was a near-death reputational crisis.

Competition from Microsoft Teams and Google Meet intensified. Both companies bundled video calling for free into products that hundreds of millions of people already used.

Microsoft Teams integrated directly into Office 365. Google Meet was built into Gmail.

Zoom had to compete against free products from two of the richest companies on Earth.

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.

Zoom

Zoom Meetings is the core — video calls that actually work. Zoom Webinars handles large-scale events with up to 50,000 attendees.

Zoom Phone is a full cloud-based phone system replacing traditional office phones. Zoom Rooms turns physical conference rooms into one-click video meeting spaces.

Zoom Contact Center competes with established call center software. Zoom Team Chat is their Slack/Teams competitor.

Zoom Whiteboard is a collaborative digital canvas. Zoom Revenue Accelerator uses AI to analyze sales calls.

And Zoom AI Companion summarizes meetings and drafts messages.

Robinhood

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

Zoom

Sequoia Capital, Emergence Capital, Horizons Ventures (Li Ka-shing), Qualcomm Ventures