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Hey — It’s Nico.
Welcome to another Failory edition. This issue takes 5 minutes to read.
If you only have one, here are the 5 most important things:
If your startup sells to big companies, check today’s sponsor: Delve helps startups finish their SOC 2 process in 15 hours (not 15 weeks). And they’re offering a $1k off promo using code FAILORY1k!
How a missing SOC 2 killed $500k in ARR.AD
This one will sound familiar: it starts with a signed enterprise intent letter… and ends with an awkward “we’ll circle back next fiscal year.”
When you’re selling into big companies, the sales and compliance process can make or break your startup — and you usually don’t realize how painful it gets until you’re already in the thick of it. Here’s the body count:
Day 1: Enterprise deal - vendor security review arrives—80+ controls, 300 questions.
Day 30: Platform only at 40%, CTO still screenshot‑hunting; sales team sweating quota.
Day 60: Deal tabled, revenue evaporates, morale shot.
Lesson learned: Speed kills—or saves. Delve users finish the entire SOC 2 process in 15 hours, not 15 weeks, because:
Incredibly simplified workflow built for founders.
AI features to make the process lightning fast.
Delve managed audit done in 10 days or less.
Outcome:
Lovable closed SOC 2 in days.
Bland closed $500kk in ARR.
Sully got 8 frameworks under their belt.
Ready to script a different ending to your SOC 2?
🔗 Resources
📰 News
Snap acquires Saturn, a social calendar app for high school and college students.
💸 Fundraising
Better Auth, an authentication tool, raises $5M.
DotCom Giants
Two of the most iconic names in online recruiting are gone.
The filing is part of a last-ditch attempt to sell off what’s left. They’re listing up to $100 million in assets and up to $500 million in liabilities. The most recognizable piece — their job boards — is getting sold to JobGet, a startup focused on hourly and gig workers.
It’s a messy end for two companies that used to be the future.
What Was CareerBuilder+Monster:
If you were job hunting anytime between 2000 and 2010, you probably landed on CareerBuilder or Monster. They weren’t just big — they were the job market online.
Monster was especially early to the game. Founded in the mid-90s, it was one of the first commercial websites on the internet, scraping job listings from newspapers and posting them online. At its peak, Monster was valued at over $8 billion, with its stock hitting $91.
CareerBuilder rose in the same era. For a while, it was the top job site in the U.S., pulling ahead of print listings and attracting millions of job seekers. From 2000 to 2010, it was everywhere — powering job search sections on hundreds of news sites and partnering with big-name employers.
Both platforms helped to move job hunting from print to digital. But they never figured out the next step.
By the 2010s, the internet had changed. Social networks were taking over, and LinkedIn was perfectly positioned for the shift. It wasn’t just a job board — it knew who you were, who you worked with, what roles you were likely to want next. Employers suddenly had tools that could surface passive candidates, build talent pipelines, and run targeted outreach. None of that was possible with a basic job listing.
Monster tried to compete by launching Monster Networking — basically a paid LinkedIn — but it flopped. CareerBuilder tried pivoting to HR tech, but it was late to the party and couldn’t catch up.
By 2024, both were struggling. So they merged.
But it wasn’t a comeback. It was a life raft.
The Numbers:
🏁 Monster launched in 1994. CareerBuilder followed in 1995.
🤝 Merged in early 2024 to stop the bleeding.
📉 Revenue in 2024 dropped 40%, down to $49.2 million.
🧾 Filed for Chapter 11 bankruptcy in June 2025.
Reasons for Failure:
They lost to LinkedIn: LinkedIn didn’t just post jobs — it mapped the professional world. Real profiles, real connections, real-time updates. That meant better matching, smarter targeting, and access to passive talent. Meanwhile, Monster and CareerBuilder were just databases of resumes. People only visited when they needed a job, and they left nothing behind. No identity, no engagement, no data. In a hiring market that became all about precision and pipelines, that wasn’t even a fair fight.
Too late to change: By the time it was clear LinkedIn had won, it was already too far ahead. Monster tried to copy it with a paid networking feature, but nobody wants to switch social networks — especially not to a worse, paid version. CareerBuilder made its own pivots, but by then, the market had moved on.
The merger solved nothing: CareerBuilder and Monster were both losing — just in slightly different ways. Merging didn’t fix their tech, improve the product, or change their position in the market. It just delayed the inevitable. When two outdated playbooks get stapled together, you don’t get innovation — you get more bloat.
They stayed broad when the market went niche: Job boards aren’t dead — they’ve just gone specialized. RemoteOK owns remote tech jobs. JobGet is all-in on hourly workers. These platforms win because they know their audience and build features tailored to them. Monster and CareerBuilder never picked a lane.
Why It Matters:
Product-market fit doesn’t last. What worked in 2005 can absolutely fail in 2025. You have to keep evolving — or you get left behind.
Distribution without defensibility is fragile. If you don’t own your users or your data, someone else will take them.
Focus is a growth strategy. In crowded markets, focusing on a niche can help you win.
CLI Agents
This week, Google quietly released something new: Gemini CLI — a command-line tool that gives you access to Gemini’s coding, research, and content generation powers, right from your terminal.
No fancy UI. No IDE. Just you, your command line, and a surprisingly powerful AI agent that can write code, fix bugs, run commands, manage tasks, and pull in real-time info from the web.
If that sounds familiar, it’s because these CLI Agents are becoming more common. And that’s the interesting part.
Why It Matters:
It’s free and insanely generous — probably the best free option to try agentic coding today.
It’s part of a bigger trend — AI agents moving from IDEs to the command line.
It’s competition — and companies like Cursor, Claude, and Windsurf should be paying attention.
Google CLI
Gemini CLI is Google’s new open-source AI agent for the terminal. It’s built on Gemini 2.5 Pro, which means it can handle long context (up to 1 million tokens), reason through complex problems, and generate everything from Python scripts to marketing blurbs.
It comes packed with tools:
It integrates with Google Search, so it can fetch live info and use it as context.
It supports the Model Context Protocol (MCP), so you can give it real-time data and documents.
It connects to Veo and Imagen, letting you generate video and images.
It’s customizable, scriptable, and works inside existing workflows.
The best part? It’s free through a Gemini Code Assist license. You get up to 1,000 model requests per day, which is significantly more than what anyone else is offering for free. This isn’t a limited trial. It’s actually usable out of the box.
If you’re a developer who prefers to work in the terminal, this is a real alternative to tools like Cursor. And it’s open-source under Apache 2.0, so you can audit the code yourself.
Claude Code
Gemini CLI isn’t the only player. Claude Code has been gaining a lot of traction in dev circles recently.
It lives in your terminal too. You point it to your codebase, and it understands your architecture, edits your files, fixes bugs, runs tests, handles Git commands — all via natural language.
It’s fast, flexible, and integrates well with existing workflows. Many devs say Claude is just better at actual coding. Cleaner suggestions. Fewer dumb mistakes. A solid alternative to Cursor if you’re okay with losing the IDE.
But here’s the problem: it’s expensive. That’s been the biggest complaint. There’s no real free tier. You’re either in or out. And for indie hackers or early-stage teams, the cost adds up quickly.
Google just undercut that completely. Gemini CLI might not match Claude’s coding quality (yet), but it’s good enough — and free. That changes the equation.
The Trend
This is what’s really happening: we’re watching AI companies build agentic coding tools for the terminal — and skip the whole IDE playbook entirely.
They’re not trying to beat Cursor at its own game. They’re building something different — leaner, faster, closer to where many devs already live.
For devs who swear by VIM or spend their life in the terminal, this makes total sense. No bloat. No distractions. Just AI agents that work with your existing tools.
At the same time, this is a cheap way for companies like Google and Anthropic to get into the agentic coding race without spending years building full IDEs. Cursor and Windsurf still have the UX advantage — and that matters — but CLI agents are catching up fast. And for many developers, especially the more technical ones, that’s enough.
What makes Google’s move so strategic is pricing. Offering so much for free puts pressure on everyone else. Cursor’s free tier is limited. Claude Code has no free tier. Gemini CLI? It gives you more room to experiment, build, and break things — without reaching for your wallet.
That's all of this edition.
Cheers,
Nico
