Compare / Block (Square) vs Pinterest
BLOCK (SQUARE)
Jack Dorsey — the guy who was already running Twitter — started a second company because his friend who was a …
Ben Silbermann built a virtual pinboard for collecting pretty pictures and accidentally created one of the mos…
AT A GLANCE
FUNDING HISTORY
Block (Square)
BUSINESS MODEL
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.
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.
HOW THEY STARTED
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.
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.
HOW THEY GREW
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.
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.
THE HARD PART
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.
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.
THE PRODUCTS
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.
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.
WHO BACKED THEM
Block (Square)
Khosla Ventures, Sequoia Capital, Kleiner Perkins, Visa, Goldman Sachs, GIC (Singapore)
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.