Block (Square)

Zoom

Block (Square)

Block makes money across several business lines. Square (the seller ecosystem) charges merchants a flat percentage per transaction — 2.6% + $0.10 for in-person payments, higher for online.

Cash App takes a fee on instant deposits, Bitcoin trading, and Cash App Pay transactions. Afterpay (announced at $29 billion in 2021, though Block's share price fell so far before closing in January 2022 that the final price was closer to $14 billion) earns merchant fees on buy-now-pay-later transactions.

TIDAL is the music streaming service (acquired from Jay-Z). Block also earns Bitcoin revenue — Cash App is one of the largest Bitcoin brokers in the US, though margins on BTC trading are razor-thin.

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.

Block (Square)

The origin story starts with Jim McKelvey, a glass blower in St. Louis and old friend of Jack Dorsey.

In 2009, McKelvey lost a $2,000 sale on a glass faucet because he couldn't accept credit cards. The customer wanted to pay with Amex.

McKelvey couldn't process it. The sale fell through.

McKelvey called Dorsey, who had been pushed out of the Twitter CEO job the year before and was serving as its chairman, and they started brainstorming. The problem was obvious: millions of small businesses, street vendors, farmers market sellers, and independent contractors couldn't accept credit cards because merchant accounts required monthly fees, credit checks, and clunky hardware that cost hundreds of dollars.

Dorsey and McKelvey wanted to make it so anyone could accept a credit card using just their phone.

They built a tiny white card reader that plugged into a smartphone's headphone jack. The reader cost almost nothing to manufacture and Square gave it away for free.

The software was simple — swipe the card, enter the amount, the customer signs on the screen, done. Square charged a flat 2.75% per transaction with no monthly fees, no contracts, and no minimums.

The product launched in 2010 and spread through small businesses like wildfire.

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.

Block (Square)

Square grew by giving away the hardware. The card reader was free.

That eliminated the biggest barrier for small businesses. A food truck operator, a yoga instructor, a farmers market vendor — anyone could start accepting cards in five minutes without spending a dollar upfront.

Square made its money on the transaction fees that followed.

The simplicity was the pitch. Traditional merchant services involved contracts, monthly minimums, tiered pricing, and hidden fees that required a finance degree to understand.

Square charged one flat rate for everything. No surprises.

That transparency built enormous trust with small business owners who had been burned by traditional processors.

Cash App grew through peer-to-peer payments and a brilliant viral strategy. The app launched in 2013 as a simple way to send money to friends.

Rappers, influencers, and content creators started using their $cashtag for tips and payments. Cash App sponsored hip-hop events and partnered with musicians.

By 2024, Cash App had over 55 million monthly active users — more than most banks.

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.

Block (Square)

The Afterpay acquisition was controversial. Announced at $29 billion in 2021, it closed in January 2022 at roughly half that after Block's own stock fell.

Buy-now-pay-later was already facing regulatory scrutiny and growing delinquency rates. Critics argued Dorsey overpaid at the peak of the market.

Afterpay's revenue growth slowed significantly after the acquisition, and write-offs on bad consumer debt increased. It remains the biggest bet Block has ever made.

The Bitcoin obsession worries investors. After renaming Square to Block in December 2021, Dorsey went all-in on Bitcoin — investing company cash in BTC, building Bitcoin mining hardware, and creating TBD (a Bitcoin-focused developer platform).

While Cash App's Bitcoin revenue is huge on paper ($10+ billion annually), the margins are tiny. Investors question whether the Bitcoin focus distracts from the core payments business.

Competition is intense on every front. Square competes with Stripe, Toast, and Clover for merchants.

Cash App competes with Venmo, Zelle, and Apple Pay for consumers. Afterpay competes with Klarna, Affirm, and bank-native BNPL products.

Block has to fight multiple wars simultaneously with finite resources.

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.

Block (Square)

Square is the merchant ecosystem — point-of-sale hardware, payment processing, invoicing, payroll, loans, and online stores for businesses of all sizes. Cash App is the consumer side — peer-to-peer payments, direct deposit, investing, Bitcoin buying, and the Cash App Card (a debit card).

Afterpay is the buy-now-pay-later product — split any purchase into four interest-free payments. Square Banking offers business checking accounts and loans.

Square Online lets merchants build e-commerce websites. TIDAL is the music streaming platform that pays artists higher royalties.

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.

Block (Square)

Khosla Ventures, Sequoia Capital, Kleiner Perkins, Visa, Goldman Sachs, GIC (Singapore)

Zoom

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