AT A GLANCE

Robinhood
Pinterest
2013
Founded
2010
Menlo Park, California
HQ
San Francisco, California
$5.6 Billion
Total Raised
$1.5 billion
Vlad Tenev & Baiju Bhatt
Founder
Ben Silbermann, Paul Sciarra, Evan Sharp
Fintech
Type
Social Media
Public (NASDAQ: HOOD)
Status
Public (NYSE: PINS)

FUNDING HISTORY

Robinhood

Seed2013
$3M raised$15M val.
Series A2014
$13M raised$60M val.
Series B2015
$50M raised$250M val.
Series C2017
$110M raised$1.3B val.
Series D2018
$363M raised$5.6B val.
Series F/G2020
$800M raised$11.2B val.
Emergency Raise + IPO2021
$3.4B raised$32.0B val.

Pinterest

Series A2011
$10M raised$40M val.
Series B2012
$100M raised$1.5B val.
Series D2013
$225M raised$3.8B val.
Series G2015
$367M raised$11.0B val.
IPO2019
$1.4B raised$12.7B val.

BUSINESS MODEL

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.

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.

HOW THEY STARTED

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.

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.

HOW THEY GREW

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.

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.

THE HARD PART

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.

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.

THE PRODUCTS

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.

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.

WHO BACKED THEM

Robinhood

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

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.

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