How Catalina Inspired
a Revolution
The journey from watching a brilliant assistant waste time on repetitive tasks to building a solution that transforms administrative work everywhere.
The Daily Grind
Every morning at 7 AM, my executive assistant Catalina would sit down at her computer and face the same overwhelming reality: dozens of emails requiring thoughtful, personalized responses. And these weren't simple "thank you" notes—they were complex communications requiring context, relationship awareness, and my specific communication style.
I watched one of the most capable professionals I know spend 3-4 hours daily on tasks that followed predictable patterns:
- "Can Jason speak at our event?" (Check calendar, provide availability, send speaking requirements)
- "Following up on our meeting" (Reference specific discussion points, outline next steps)
- "Quick question about the project" (Review project status, provide contextual update)
Catalina could have been planning strategic initiatives, managing complex projects, or building key relationships. Instead, she was essentially a very expensive email composer.
The Lightbulb Moment
The breakthrough came during a particularly busy week when I had three conferences, two board meetings, and a product launch. Catalina was drowning in email, and I could see the frustration building.
She's brilliant—she could be running operations for a Fortune 500 company. Yet here she was, typing variations of the same responses she'd written hundreds of times before.
That's when I realized: if patterns are predictable, they're automatable.
Catalina's Weekly Reality
Building the Solution
As someone who's spent years in technology and business operations, I knew this problem was solvable. But I didn't want to build just another generic automation tool. I wanted to create something that understood context, maintained relationships, and preserved the human touch that makes Catalina so effective.
We started with a simple question: "What if AI could handle the routine responses, leaving Catalina free for the strategic work only she can do?"
The First Success
Three months later, we had our first working prototype.
Before AI Email Drafter
After AI Email Drafter
The AI didn't replace her—it amplified her capabilities.
Why "Cheaper Than Karen"?
The name started as an inside joke. During development, someone mentioned that the AI was "literally cheaper than hiring another Karen from accounting to help with emails." We laughed, but the truth stuck: this automation costs a fraction of another salary, works around the clock, and gets better over time.
It's not about replacing people—it's about freeing great people from mundane tasks so they can do great work.
Sharing the Solution
What began as a personal productivity hack for my office became something bigger when other executives started asking, "How did you clone Catalina?" They weren't seeing more of her—they were seeing her working on higher-value activities because the routine stuff was handled automatically.
That's when we realized this wasn't just our solution—it was a solution the entire EA and VA community needed.
Our Mission Today
Every executive assistant, virtual assistant, and administrative professional deserves to work on meaningful projects that showcase their intelligence and drive business results. They shouldn't be stuck in email prison, crafting the same responses over and over.
CheaperThanKaren.com exists to automate the routine so human intelligence can focus on what actually matters. We're building tools that make assistants more valuable, not replaceable.
What We're Building
Meet the Team
Technology executive turned productivity obsessive. After watching too many brilliant assistants waste time on automatable tasks, I decided to do something about it. When not building automation tools, you can find me planning the next strategic project with Catalina (who now has time for the interesting stuff).
Catalina
Head of User Experience & Original Guinea Pig
The inspiration behind everything we build. Catalina ensures that every tool we create actually makes assistants' lives better, not more complicated. Her feedback drives our product development because if it doesn't work for her, it doesn't ship.
If something we build doesn't pass the "Catalina test" - meaning it doesn't actually save her time or improve her work quality - we don't release it.
What's Next
This started as a solution for one assistant's email overwhelm and has become a mission to transform how businesses think about administrative automation. We're building a complete suite of tools that will automate the routine so human intelligence can focus on what actually matters.
Smart Calendar Management
Automated scheduling that actually understands preferences
Meeting Prep Automation
Briefing documents that write themselves
Follow-up Systems
Never let anything fall through the cracks again
Document Processing
AI that reads, summarizes, and organizes like your best intern
Our Commitment
Every tool we build will be tested in our own operation first. If it doesn't make Catalina's workday better, it doesn't get released. If it doesn't provide clear economic value, it doesn't get built. If it doesn't solve a real problem that real assistants face, it doesn't make it past the idea stage.
We're not just building software—we're building the future of administrative work, where human creativity and strategic thinking are supported by intelligent automation instead of buried under routine tasks.
Because the best assistants shouldn't be doing assistant work—they should be doing strategic work that happens to include some assistance.
Ready to Join Our Mission?
Help us transform administrative work by starting with your own email automation. Experience the same transformation that freed Catalina to do her best work.
Join the revolution that started with one frustrated assistant and is now transforming workdays everywhere.