Patreon

Sierra

Patreon

Patreon takes a percentage of every payment processed through the platform. It used to run three tiers — 5%, 8% and 12% depending on how many features a creator wanted — and creators who signed up back then are still on those rates.

Everyone joining now pays a flat 8%.

On top of the platform fee, payment processing fees (typically 2.9% + $0.30 per transaction) are passed to either the creator or patron depending on the plan. The combined take rate means Patreon captures roughly 8-15% of the money flowing through the platform.

The business scales beautifully. More creators attract more patrons.

More patrons increase creator earnings. Higher earnings attract more creators.

And Patreon's cut grows proportionally with every dollar processed. Creators have been paid more than $8 billion through the platform since it launched in 2013.

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.

Patreon

Jack Conte was one half of Pomplamoose, an indie music duo that went viral on YouTube in the late 2000s. Their cover of Beyoncé's "Single Ladies" got millions of views.

Their original music was critically praised. And they were barely making enough to pay rent.

The math was brutal. A million YouTube views paid about $1,500 in ad revenue.

Conte spent weeks producing high-quality music videos that cost thousands to make. The economics didn't work.

YouTube's ad model paid creators fractions of a penny per view. Spotify paid fractions of a penny per stream.

For mid-tier creators — popular enough to have a real audience but not famous enough for brand deals — the internet was a machine that turned creative labor into pennies.

In 2013, Conte teamed up with Sam Yam, a college roommate and developer at AdRoll. Their idea was simple: let fans pay creators directly through monthly subscriptions.

Not per-video donations. Not tips.

Recurring monthly payments — like a Netflix subscription but for individual creators. They called it Patreon, from "patron of the arts." The platform launched in May 2013 and signed up its first creator the same week.

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.

Patreon

Patreon grew through creator evangelism. When a podcaster or YouTuber told their audience "support me on Patreon," that was free marketing to exactly the right audience.

Every creator who joins becomes a distribution channel.

The platform expanded beyond its indie roots by courting bigger creators. Podcasters were the first breakout category — shows like Chapo Trap House, True Crime Obsessed, and Last Podcast on the Left built six-figure monthly incomes on Patreon.

Then YouTubers, writers, musicians, and visual artists followed.

International expansion drove the next phase. Patreon now supports payments in multiple currencies and serves creators in over 180 countries.

The creator economy is global — a manga artist in Japan can have patrons in Brazil paying in US dollars, processed through Patreon seamlessly.

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.

Patreon

Platform risk is the core vulnerability. Patreon is entirely dependent on creators choosing to use it.

If YouTube, Instagram, or TikTok build sufficiently good subscription tools (YouTube Memberships already exists, Instagram Subscriptions launched), creators might consolidate onto the platforms where their audiences already live. Why send fans to Patreon when they can subscribe directly on YouTube?

The moderation challenge is constant. Patreon hosts content across the entire creative spectrum — including adult content, political commentary, and controversial creators.

Payment processors (Stripe, PayPal) have their own content policies and have pressured Patreon to remove creators. Every moderation decision risks alienating a segment of the creator community.

Revenue concentration is a risk. A relatively small number of top creators generate a disproportionate share of Patreon's revenue.

If a handful of the biggest creators leave for a competing platform or build their own subscription tools, it would materially impact Patreon's business.

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.

Patreon

Patreon Memberships — the core product allowing creators to offer tiered monthly subscriptions with exclusive content, early access, behind-the-scenes material, and community perks. Patreon Commerce — tools for selling digital downloads, merchandise, and one-time purchases directly to fans.

Patreon Community — Discord-style community features built natively into Patreon, including chat, posts, and polls for patron-only spaces. Patreon Video — native video hosting so creators can post exclusive content directly on Patreon instead of using unlisted YouTube links.

Patreon Free Membership — a free tier that lets fans follow creators and access some content, serving as a conversion funnel to paid tiers.

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.

Patreon

Index Ventures led the Series A. Tiger Global led the 2021 round that valued Patreon at $4 billion.

Tiger Global participated in growth rounds. Initialized Capital was an early backer.

DFJ Growth and Wellington Management invested in later rounds. Creators themselves, including YouTubers and podcasters, have been informal ambassadors and some have invested personally.

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.