Coinbase

Sierra

Coinbase

Coinbase makes money from transaction fees. Every time someone buys or sells crypto on the platform, Coinbase takes a cut — typically around 1.5% for regular users, lower for high-volume traders on its advanced trading tier.

For a company that processes billions in daily volume, that adds up fast. In the 2021 bull run, Coinbase generated $7.8 billion in revenue.

Beyond trading fees, Coinbase earns revenue from staking (users earn yield on their crypto, Coinbase takes a commission), USDC interest (Coinbase co-created the USDC stablecoin with Circle and earns interest on the reserves), custodial services for institutions, and its cloud platform for developers building on-chain apps.

Sierra

Companies pay Sierra to run their customer service with AI agents instead of hiring rooms full of humans. The agent talks to your customers over chat.

It answers questions. It processes returns.

It updates subscriptions. Here is the clever part.

Sierra charges based on outcomes, not seats. Brands pay when the AI actually resolves a problem, not just for having the software installed.

That pricing is unusual. Most software charges a flat monthly fee no matter what.

Sierra only gets paid when the bot does the job.

Coinbase

Brian Armstrong was working as a software engineer at Airbnb in 2010 when he read Satoshi Nakamoto's Bitcoin white paper. He became obsessed.

At the time, buying Bitcoin meant navigating sketchy exchanges, wiring money to anonymous accounts, and hoping your coins didn't get stolen. Armstrong thought: this is never going mainstream unless someone makes it dead simple.

In 2012, Armstrong got into Y Combinator and co-founded Coinbase with Fred Ehrsam, a former Goldman Sachs trader. Their pitch was straightforward — be the easiest, safest, most regulated way to buy and sell Bitcoin.

While other crypto exchanges were operating in legal gray areas, Coinbase went out of its way to get money transmitter licenses in every US state. It was slow and expensive, but it meant Coinbase was the one exchange your bank wouldn't block.

The first version was bare-bones. You linked your bank account, bought Bitcoin, and Coinbase held it for you.

That custody model — Coinbase holding your crypto — was controversial with crypto purists who preached "not your keys, not your coins." But for normal people who didn't want to manage private keys, it was exactly what they needed.

Sierra

Bret Taylor had already done the impossible twice. He co-created Google Maps.

He later became co-CEO of Salesforce, chaired Twitter's board during the messy Elon Musk takeover, and became chairman of OpenAI in late 2023. Clay Bavor spent 18 years at Google, most recently running its Labs group.

The two friends left their big jobs in 2023 to build something together. They picked customer service on purpose.

It is the least glamorous corner of software. Their logic was simple.

Companies hate their support costs. Customers hate waiting on hold.

AI that actually resolves problems could fix both sides at once. They launched Sierra in February 2024 with $110 million from Sequoia and Benchmark.

Coinbase

Coinbase grew with the Bitcoin price cycle. Every bull run brought a wave of new users who heard about crypto from the news or their friends and Googled "how to buy Bitcoin." Coinbase was almost always the first result.

The company spent heavily on brand advertising including a legendary Super Bowl ad in 2022 that was just a bouncing QR code — it crashed the app from the traffic surge.

The regulatory strategy was the long game. While Binance and FTX grew faster by ignoring regulations, Coinbase spent years and millions getting licensed.

When the regulatory crackdown came, Coinbase was the last exchange standing. Being "the regulated one" went from a competitive disadvantage to the only thing that mattered.

The direct listing in April 2021 was a landmark moment. Coinbase went public via direct listing at a $85 billion valuation — the largest direct listing in history at the time.

It legitimized crypto as an asset class in a way that no Bitcoin price chart ever could.

Sierra

Sierra went straight for big brands, not tiny startups. SoFi, Ramp, ADT, Sonos and Brex signed up early.

By 2026 it said more than 40% of the Fortune 50 were customers. The trick was trust.

Enterprises are terrified of an AI bot going rogue and insulting a customer. So Sierra built guardrails and let each company control exactly how the agent behaves.

Bret Taylor's contacts did the rest. When the chairman of OpenAI calls a Fortune 500 CEO, they pick up.

Sierra hit $100 million in annual recurring revenue in November 2025, seven quarters after launch, and $150 million by February 2026. In April 2026 it launched Ghostwriter, which builds and deploys a new agent from a plain-English description.

Coinbase

The crypto winter of 2022 nearly broke the company. After the collapse of FTX, Luna, and Three Arrows Capital, crypto trading volume fell off a cliff.

Coinbase's revenue dropped from $7.8 billion in 2021 to $3.1 billion in 2022. The stock went from $342 to $35, a 90% decline.

Armstrong laid off 18% of the company in June 2022 and another 20% in January 2023.

The SEC lawsuit was existential. In June 2023, the SEC sued Coinbase alleging that it operated as an unregistered securities exchange.

The lawsuit claimed that at least 13 crypto assets traded on Coinbase were securities. If the SEC won, it could have fundamentally broken Coinbase's business model.

The SEC dropped the case entirely in February 2025, dismissing it with no penalty and no admission that any token was a security.

Revenue concentration is a structural risk. Coinbase's revenue swings wildly with crypto prices and trading volume.

In bull markets, the company prints money. In bear markets, revenue evaporates.

This makes it nearly impossible to plan long-term or maintain consistent growth — Wall Street hates unpredictability.

Sierra

Everyone is building AI customer service agents right now. Decagon has raised at a multi-billion valuation.

Salesforce, ServiceNow and Intercom all shipped their own agents. Sierra is not the cheap option.

It sells premium AI to giant companies that move slowly. The bigger risk sits underneath the product.

Sierra does not make its own AI models. It rents them from providers like OpenAI and Anthropic.

If those model makers decide to compete directly, Sierra's edge gets thin fast, and its co-founder chairing one of them only makes that question louder. A $15.8 billion valuation on roughly $150 million in revenue leaves almost no room for a stumble.

Coinbase

Coinbase is the consumer trading platform — buy, sell, and hold 250+ cryptocurrencies. Coinbase Advanced Trade (formerly Coinbase Pro) is the lower-fee, more sophisticated trading interface.

Coinbase Wallet is a self-custody wallet where users control their own keys. Coinbase Prime is the institutional platform for hedge funds, family offices, and corporations.

Base is Coinbase's own Layer 2 blockchain built on Ethereum, designed for cheap, fast transactions. USDC is the stablecoin Coinbase co-created with Circle — pegged 1:1 to the US dollar with over $30 billion in circulation.

Coinbase Commerce lets businesses accept crypto payments.

Sierra

The core product is the Sierra AI agent. It is a branded customer service bot that companies deploy on their website, app, and phone lines.

It handles the boring stuff. Order tracking.

Refunds. Password resets.

Account changes. Sierra also built its own tools to test and monitor these agents so they do not make things up.

In 2024 the company added a voice version that talks to customers on the phone. In April 2026 it added Ghostwriter, a tool that builds and deploys a new agent from a plain-English description.

The whole pitch is one AI agent that carries your brand's name and never sleeps.

Coinbase

Y Combinator, Andreessen Horowitz, Union Square Ventures, Tiger Global, Ribbit Capital, IVP

Sierra

Sequoia Capital and Benchmark wrote the first checks at launch in February 2024, $110 million between them. Greenoaks Capital then led both the $175 million round in 2024 and the $350 million round in September 2025.

In May 2026 Tiger Global and Google's GV led a $950 million round at a $15.8 billion valuation, with Benchmark, Sequoia and Greenoaks back in. That takes total funding to about $1.6 billion.

That is partly the product and partly Bret Taylor. Investors bet on founders who have already built billion-dollar things.