Slack

Discord

Slack

Slack uses a freemium model. The free tier gives you access to your most recent 90 days of messages and 10 app integrations.

That's enough to get hooked. Then Slack charges per user per month — $8.75/month for Pro, $15/month for Business+, and custom pricing for Enterprise Grid.

The beauty of the model is that one person signs up, invites their team, the team gets addicted, and suddenly the company is paying for 500 seats. It's a virus that charges rent.

Discord

Discord makes money primarily through Nitro — a $9.99/month subscription that gives users bigger file uploads, HD video streaming, custom emoji, animated avatars, and profile customization. There's also Nitro Basic at $2.99/month with fewer perks.

Server owners can pay for Server Boosts that unlock premium features for their community. Discord also added a cut of server subscriptions — creators can charge monthly membership fees and Discord takes 10%.

The key insight is that Discord's core product is completely free. Voice chat, text chat, screen sharing, communities with thousands of members — all free.

Nitro is cosmetic and convenience upgrades. Most users never pay and Discord is fine with that.

The free users create the network effects that make the platform valuable.

Slack

Stewart Butterfield had already done this exact thing once before. In 2002, he was building a massively multiplayer online game called Game Neverending.

The game flopped but one of its features — a photo-sharing tool — became Flickr, which Yahoo bought for $35 million in 2005.

So in 2009, Butterfield did it again. He started a company called Tiny Speck to build another game called Glitch — a quirky, non-violent MMO where players collaborated instead of fighting.

The game was beautiful, weird, and a complete commercial failure. It shut down in November 2012 after never finding a big enough audience.

But the internal communication tool the Glitch team had built for themselves was something special. They had created a searchable, organized messaging system because email was driving them insane.

Every conversation was in channels. Everything was searchable.

Files were shared inline. It was everything email should have been but wasn't.

Butterfield looked at this internal tool and thought: this is the actual product. In August 2013, Slack launched in preview.

Within 24 hours, 8,000 companies had signed up. Within two weeks, it was 15,000.

The growth was so fast that Butterfield said it felt like "trying to drink from a fire hose."

Discord

Jason Citron had already built and sold a gaming company — OpenFeint, a social gaming platform for mobile, which GREE bought for $104 million in 2011. After that, he started Hammer & Chisel, a game studio that was supposed to make mobile games.

The game they built, called Fates Forever, was a mobile MOBA that got great reviews but almost nobody played.

What Citron noticed was that gamers were using terrible tools to communicate. TeamSpeak was clunky.

Skype was laggy. Nothing worked well for groups of people who needed to talk while gaming.

The internal voice and text chat tool that Hammer & Chisel had built for their own team worked better than anything on the market.

Citron and co-founder Stan Vishnevskiy pivoted the entire company. They stripped out the gaming stuff and launched Discord in May 2015 as a free voice, video, and text chat platform for gamers.

It spread through Reddit first — a post on the r/gaming subreddit went viral and crashed their servers on day one. Within a year they had 25 million registered users.

Slack

Slack grew almost entirely bottom-up. Nobody sold Slack to companies.

Employees adopted it on their own and then convinced their bosses to pay for it. One developer would start using the free version, invite their team, and within weeks the whole department was hooked.

IT departments would discover that half the company was already on Slack before anyone asked for approval.

The integrations strategy was genius. Slack made it dead simple for other software tools to plug into Slack.

Instead of checking Jira for bug reports, Salesforce for deals, and GitHub for code changes, everything pushed notifications into Slack. Slack became the operating system of work — the one app you kept open all day.

Word of mouth was the main growth driver. Slack didn't spend heavily on advertising early on.

They spent on making the product feel delightful. The loading messages were funny.

The emoji reactions were addictive. The search actually worked.

People genuinely liked using it, which is almost unheard of for enterprise software.

Discord

Discord grew through communities, not ads. The first users were gamers on Reddit and Twitch who were sick of TeamSpeak and Skype.

Streamers would set up Discord servers for their fans, and every viewer who joined brought their friends. The growth was entirely organic for years.

The bot ecosystem was the secret weapon. Discord made it trivially easy to build bots — automated programs that add functionality to servers.

Music bots, moderation bots, gaming bots, utility bots. Developers built tens of thousands of bots, each one making Discord servers more useful and sticky.

A server with good bots became a mini-app platform.

COVID and the "beyond gaming" shift were massive. When lockdowns hit, study groups, book clubs, art communities, crypto communities, and just friend groups all started using Discord.

By 2020, non-gaming usage overtook gaming usage. Discord quietly dropped the "for gamers" tagline and rebranded as a platform for communities of all kinds.

Slack

Microsoft Teams was the existential threat. When Microsoft bundled Teams for free with Office 365 in 2017, Slack knew it was in trouble.

Microsoft had 300 million Office users who could start using Teams without paying anything extra. Slack even took out a full-page newspaper ad welcoming Microsoft to the chat market — a bravado move that masked genuine fear.

By 2020, Teams had overtaken Slack in daily active users purely on distribution.

The pandemic was a double-edged sword. Remote work exploded demand for Slack, but it also exploded demand for Teams, Zoom, and every other collaboration tool.

Slack's growth accelerated but so did everyone else's. The window where Slack was the obvious default was closing.

Revenue growth started slowing. After years of 50%+ annual growth, Slack's growth rate dropped to the low 30s by 2020.

Wall Street punished the stock, which dropped from its IPO price. The writing was on the wall — Slack couldn't outrun Microsoft alone.

In December 2020, Salesforce announced it was acquiring Slack for $27.7 billion. Butterfield stayed on as CEO until 2023, then left.

Discord

Monetization has been the eternal question. Discord has 200 million monthly active users but has never turned a profit.

Nitro subscriptions are growing but most users are happy on the free tier. Unlike Facebook or Twitter, Discord doesn't run ads — they've explicitly said ads in DMs or chat would destroy the product.

Finding ways to monetize without betraying user trust is the core challenge.

The Microsoft acquisition saga. In early 2021, Microsoft reportedly offered $12 billion to buy Discord.

Citron and the board walked away. The thinking was that Discord could grow into something worth much more independently.

Whether that was the right call depends on whether Discord can eventually figure out profitability — Microsoft would have solved that problem instantly with its distribution.

Content moderation at scale is brutal. With millions of servers and hundreds of millions of users, Discord has struggled with harmful content — extremist groups, CSAM, doxxing, and harassment.

They've invested heavily in trust and safety teams and automated detection, but the decentralized nature of servers makes moderation much harder than a centralized feed like Twitter or Facebook.

Slack

Slack is the core messaging platform — channels for teams, direct messages, threads for focused discussion, and huddles for quick voice/video calls. Slack Connect lets you message people at other companies directly through Slack instead of email.

Slack Canvas is a built-in document editor for notes and wikis right inside channels. Workflow Builder lets non-technical users automate repetitive tasks without writing code.

The App Directory has 2,600+ integrations — connect Google Drive, Salesforce, Jira, GitHub, or basically any tool your company uses.

Discord

Discord's core is servers — community spaces organized into text and voice channels. Think of a server like a clubhouse with different rooms for different topics.

Voice Channels let you drop in and out of audio conversations like a walkie-talkie. Stage Channels are for live audio events with audiences.

Forum Channels organize discussions by topic. Discord also has direct messaging, group chats, video calls, screen sharing, and a growing app/bot ecosystem.

Activities let users play games and watch videos together inside Discord calls.

Slack

Accel Partners, Andreessen Horowitz, Social Capital, GV (Google Ventures), SoftBank, Dragoneer Investment Group

Discord

Benchmark, Accel Partners, Greylock Partners, Index Ventures, Greenoaks Capital, Dragoneer Investment Group, Spark Capital, Fidelity Investments