I joined Reddit in my twenties because I couldn’t stand Facebook anymore.
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Facebook was curated to death... filtered photos, job announcements, people pretending their lives were more interesting than they were. Every post felt like it had an angle. Reddit didn’t.
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Reddit was raw, anonymous, chaotic. You could show up as a half-baked thought and still be heard. It wasn’t about friends or followers. It was about the ideas, the humor, the outrage, the rabbit holes you never meant to fall down.

I remember r/IAmA when it was electric. Obama popped in. So did a Domino’s delivery guy from Alaska, a death row prison guard, a guy who’d survived a bear attack. You never knew what you were going to find. But you always knew it was real. People didn’t posture on Reddit. They shared brutally, hilariously, often beautifully.

It felt like the last honest place on the internet. And now it’s a public company.
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$6.4 billion valuation at IPO; $18.4B today. NYSE ticker: RDDT.

The same platform that once rallied millions to hold Wall Street hostage with GameStop is now trading next to Goldman Sachs.

You can’t make this stuff up.

Reddit was never about the company. It was about the people who showed up every day to make the internet weird, smart, and alive.
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Volunteer mods donated thousands of hours. Users wrote novel-length essays. Whole subcultures thrived without asking for anything in return.
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It was one of the only places online that felt earned — like it was being built in real time by real people, without a content strategy deck behind it.

Reddit was Wikipedia with attitude. It was the town square if the town was full of insomniacs, PhDs, dungeon masters, and chronic shitposters.

Reddit pulled in ~$800 million last year — and still burned $91 million. So they did what every platform does when the growth story starts to die: they sold the users.

Not to advertisers. To algorithms.

Reddit is now licensing its content to AI companies — OpenAI, Google, and whoever’s next — so they can train large language models on everything users ever posted. The jokes. The rants. The trauma dumps. The inside jokes and internet history people thought they were just sharing in the moment.

All of it... scraped, packaged, and monetized. Not for the mods. Not for the users. For the shareholders.

ChatGPT will soon be quoting posts from r/relationships and r/explainlikeimfive, polished into corporate emails and fake-sounding dialogue in Netflix scripts.

The irony: Reddit users spent years building something authentic. Now, that authenticity is being mined to feed machines that will replace it.

The soul of Reddit was never in the codebase or the tech. It was in the weirdness and the tangents. The feeling that you were somewhere different.
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r/creepy. r/tifu. r/nostalgia. r/wallstreetbets.

Subreddits where people showed up with no agenda, no monetization plan. Only stories, questions, sometimes total nonsense. And it worked.

It worked because there was no ROI being chased. Now I have to wonder: is that gone? Or is it just… thinning?

Mods are threatening strikes. Some of the most beloved subreddits have gone dark in protest. Users are leaving or quietly fading out. And the energy (that raw, electric, unpredictable energy) is already leaking elsewhere.

You see it in Discord servers, where niche groups rebuild their tribes behind closed doors. You see it in Lemmy and Kbin, Reddit clones built on open-source, federated platforms with no corporate leash.
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You even feel it, strangely, in the X ecosystem, where chaos has at least been honest.

The common thread: they feel owned by the users. At least for now.

Reddit’s IPO is being celebrated as a business milestone. But culturally, it’s a turning point... a slow, silent shift where the last internet commons got carved up and sold off.

We’ve seen this movie before. Tumblr. Twitter. Digg. Communities that mattered… until they didn’t. There’s no button to push when a vibe dies. It just happens. One dark subreddit at a time. One mod burnout at a time. One user who logs out and forgets to come back.

And one day, years from now, someone will say “Remember Reddit?” And there will be a pause. A smile. And a hundred little memories of nights spent scrolling, laughing, learning — before it all got flattened into product strategy and quarterly earnings.
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You can’t really ever own a community. You can nurture it. You can host it. But the second you try to extract from it, commodify it, or sell it off in pieces… it starts to rot.

Reddit mattered because it meant something. It was weird and hard to explain and impossible to replicate. It was built by people who didn’t need to be paid to care.

The tech world talks endlessly about product-market fit. But Reddit had something deeper — community-market fit. Emotional-market fit (I talked about this in the last edition, here). That's the kind of fit that makes people give a damn... that builds lore. That lasts. If you’re building for the long term, that’s the only kind that matters.

In the end, no one will remember your quarterly numbers. But they will remember how your product made them feel.

And Reddit, for all its chaos, felt like something to a lot of people. Will it still?

Read it online »

What it all means ​
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💡 Monetizing a community is easy. Maintaining one is near impossible. Reddit didn’t fail financially. It IPO’d. On paper, it did everything right. But look closer, and you’ll see the rot: mods revolting, subs going dark, users migrating to Discord and Lemmy. Why? Because Reddit treated the community like a product. And communities can feel that. Once people sense they’re being extracted from, not built for, they start to disappear — slowly, silently, sometimes all at once. Founders confuse monetization with loyalty. But loyalty is emotional. And when you lose that, no amount of revenue will bring the soul back.

💡 Platforms built on unpaid labor eventually face an existential reckoning. Reddit was powered by millions of people giving their time, creativity, and moderation energy for free. For years, it worked because the users felt ownership — like it was theirs. But when Reddit started selling the content to train AI models and cash in through an IPO, that illusion shattered. It's a broader pattern: the internet is full of platforms quietly monetizing human effort while pretending it's a partnership. But when value extraction overtakes value creation, the backlash isn’t always loud. Sometimes it’s just… abandonment. Silent churn is still death.

💡 If you don’t protect the weirdness, the weirdness leaves. Reddit was never great because of its product. It was great in spite of it. The UI was clunky. The search was broken. But the culture? Untouchable. It had layers, in-jokes, dark corners and lightning-in-a-bottle moments you couldn’t fake. That’s what made it worth anything at all. And that’s what’s now at risk. Tech companies love to streamline, sanitize, and optimize their way into maturity — but in doing so, they often delete the very thing people came for. Weirdness isn’t a bug. It’s the moat. And when you kill it, your product becomes just another portal on the internet.

Major news

• Google's Enterprise Cloud Introduces Music-Generating AI Model. Google has launched Lyria, a text-to-music AI model, in preview for select customers, enhancing its enterprise cloud offerings with advanced audio generation capabilities. » More «
• TikTok ban delayed—but ByteDance still on the hook. Trump extended TikTok’s forced-sale deadline by 75 days, but Oracle and U.S. suitors like Amazon and Walmart are circling. » More «
• From Panic to Euphoria: The 48-Hour Market Flip. Two days ago, everyone thought the market was crashing. Then out of nowhere, everything turned green. Stocks bounced. Bitcoin jumped. It all happened because Trump paused some tariffs, and a few good headlines dropped. Then algorithms took over and started buying everything. » More «

Founder tips

📌 You don’t need equity capital. You need working capital.​
Most founders raise VC to solve cash flow timing issues — not to build some world-changing company. But revenue-based financing, factoring, and even pre-paid SaaS plans exist for exactly that. Don’t trade permanent ownership for temporary liquidity.

📌 The best fundraising deck is a term sheet from someone else.​
You don’t raise equity capital with slides. You raise it with leverage. And the fastest way to build leverage is to show other people want in. Instead of perfecting a narrative, create urgency — from a customer, a partner, a competing investor. When someone else sets the floor, the room changes.

📌 Funding doesn’t unlock focus but scarcity does.​
The constraint of limited cash forces clarity — on what matters, what converts, what actually moves the needle. Capital creates optionality, but too much too early creates noise. Your brain sharpens in a drought. Use that edge before you drown it in dollars.

Financial markets

Meaningful Market Transactions

📈 Equity Chef Robotics Secures $43M Series A ("dequity" or combination of equity and debt) 5 Agentic AI Startups Raise Combined $52M​

💳 Credit Capteris Closes $20M Deal for Railcars with Specialty Chemical manufacturer MidCap Business Credit Completes $30M Asset-Based Facility

♟️ M&A Ripple Acquires Hidden Road for $1.25B Infineon Tech Buys Marvell's Automotive Ethernet Division for $2.5B​

Recent Cirrus Term Sheets & Transactions

A couple weeks back, we closed a $4M delayed-draw term loan facility for a prominent recreational sports brand.

After 50+ attempts, we unlocked the right capital partner to fuel scale and position the firm to cross nine figures in revenue.

We also finalized a $600K term loan for a beauty brand in NYC—despite post-bankruptcy issues and very little operating history.

We moved quickly, structured around their new entity, and delivered the money in weeks to help spur their evolution.

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To your growth,

Ryan Ridgway, Founder & Managing Partner

​Cirrus Capital Partners​

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