OpenAI’s CFO says annualized revenue topped $20B in 2025. Growth has been driven by a massive jump in computing power and record user activity. The company is leaning into ads, agents, and workflow automation while keeping its balance sheet light through partnerships. Next up is practical AI adoption in health, science, and enterprise, and a first OpenAI device slated for late 2026. AI scale is officially big-business scale. (Reuters)

Trump is escalating trade threats, this time targeting French wine and champagne with a proposed 200% tariff. Trump also doubled down on plans to take control of Greenland, brushing off European resistance and hinting at more tariffs if allies push back. Markets are watching closely as trade policy, geopolitics, and off-the-cuff diplomacy collide… again. (CNBC)

TikTok is rolling out stronger age-detection tech across Europe to crack down on under-13 users. The move comes as multiple EU countries consider raising minimum social media age limits. At the same time, TikTok is making its economic case, claiming €31B in EU economic impact in 2025 and support for 6.5M businesses. Regulation is looming, but TikTok wants credit for both safety and scale. (Social Media Today)

Private equity firm Everstone Capital is combining India’s Wingify and France’s AB Tasty to create a global digital experience optimization platform with over $100M in annual revenue. The move reflects growing consolidation in A/B testing and personalization as enterprises push for AI-ready, all-in-one platforms. No layoffs are planned, just heavier investment in AI-driven capabilities ahead. (TechCrunch)

Amazon is fighting Saks Global in court, arguing its $475M investment tied to Saks’ Neiman Marcus acquisition is now worthless following Saks’ Chapter 11 filing. Originally, the deal included a “Saks at Amazon” storefront and guaranteed referral fees. Amazon warns it may seek stronger remedies, including a court-appointed trustee, as Saks begins drawing on $1.75B in new financing to avoid immediate liquidation. (Complex)

The bill has since made its rounds on LinkedIn and Reddit, with most people (myself included) stunned at the cost for just one quarter.

And this for sure prompted a lot of founders to cautiously open their own billing dashboards.

Because while that number is extreme, the feeling isn’t.

Almost every growing team hits a moment where Slack and tools like it start feeling like a tax. Headcount goes up, contractors stick around, channels multiply, and suddenly the bill is… uncomfortable.

This isn’t a “Slack is bad” take. 

Slack is still one of the best communication products ever built, and my team uses it daily.

But, I’ve got to ask, “Is Slack still the best tool for how your team actually works today or just the default you never revisited?”

Especially now that so many teams are remote, hybrid, or fully async.

So let’s talk alternatives, tradeoffs, and where each tool actually makes sense.

Best for: Remote teams that need to move fast and don’t want to think too hard about tooling.

Slack’s biggest strength is still the obvious one: it’s easy.

It’s intuitive, straightforward, and new hires don’t need onboarding to use it. That alone explains why it’s everywhere.

Everything in Slack is organized around chat, which is a double-edged sword.

Chat is great for speed. But it’s terrible as a long-term system of record.

Decisions get made quickly, but they also get buried. Then, a few months down the line, you’re scrolling through channels trying to remember why something was decided in the first place.

Our team operates fully remotely, so having a reliable communication tool isn’t optional. 

We use Slack daily for quick huddles, screen sharing, file sharing, and general coordination. For that, it does exactly what it needs to do.

What Slack does well

Where Slack starts to break down

If you’re paying more than you’d like for Slack, a quick clean-up/audit can cut down your bill. Or you can just keep reading and check out some of the alternatives. 

Best for: Teams that want fewer tools, more structure, and don’t mind a learning curve.

Some of my team and I recently migrated parts of our workflow to ClickUp for a few external projects.

And, the simplest way to describe ClickUp is this: It’s Clockify + Notion + Slack rolled into one platform.

And for the most part, it actually lives up to the “all-in-one” promise.

Where ClickUp really shines is organization. 

Tasks, docs, timelines, time tracking, dashboards, everything is in one place, which cuts down a lot of context switching.

One feature my team loves more than expected: AI Agents.

We uploaded some of our internal playbooks and processes into ClickUp. 

Now, when I ask a question about a deadline or how something should be done, the AI often answers before a teammate even sees the message. 

It’s surprisingly useful, especially for repeat questions and standard workflows.

What ClickUp does well

Where ClickUp can get frustrating

ClickUp works best when you actually want structure.

If your team just needs fast communication, it can feel like overkill.

But if you’re tired of juggling five tools and losing context across them, ClickUp can replace a surprising amount of your stack.

Best for: Companies already deep in Microsoft 365.

If your company already runs on Microsoft (Outlook, Word, Excel, SharePoint) Teams usually comes “free” with your licenses. And for a lot of finance and ops teams, that alone makes the decision.

We’ve worked with plenty of clients who use Teams simply because it was already there. 

Now, where Teams actually works well is in scheduled, structured communication:

It feels familiar to anyone who’s spent time in a corporate environment.

What Teams does well

Where Teams struggles

For fast-moving, async-heavy teams, Teams doesn’t feel like the best option, but if you're a Microsoft 365 fanatic, then this should probably be your top pick. 

Best for: Engineering-heavy teams that care deeply about security and control.

Mattermost is basically the anti-Slack.

It’s built for teams that want:

You’ll see Mattermost used a lot in:

If Slack feels too SaaS-y or risky from a data standpoint, Mattermost is usually the alternative people evaluate.

What Mattermost does well

Where Mattermost falls short

Mattermost is a great tool if your team already uses GitHub and Jira and thinks in systems.

But for sales, marketing, or ops teams, it can feel heavy and challenging fast.

Tech teams, this one is for you. 

Best for: Teams that want ClickUp-style structure with a slightly lighter learning curve.

Monday.com is one of ClickUp’s closest rivals. 

It’s built around visual workflows (Kanban boards, timelines, and dashboards) but with a cleaner, more approachable interface. 

Where ClickUp can feel overwhelming if overbuilt, Monday.com often hits a sweet spot for teams that want structure without drowning in options.

What Monday.com does well

Where Monday.com can get frustrating

Slack: Fast, intuitive chat. Great for speed, not great for long-term context.

ClickUp: All-in-one workflow powerhouse. Deep structure, but can be overwhelming.

Monday.com: Visual, structured, lighter learning curve than ClickUp, best for cross-functional teams.

Teams: Works if you’re deep in Microsoft 365; slow for async-heavy or creative teams.

Mattermost: Security-first, self-hosted option for dev-heavy teams; not intuitive for non-tech users.

At the end of the day, there’s no one-size-fits-all communication tool. 

The best tool is the one that actually fits how your team works today. 

Test a few, take advantage of free trials, see what clicks, and then commit, your future self (and your sanity) will thank you.