How I Built My AI Assistant (And What It Means for Your Business)

A few months ago, I realized I was drowning in administrative tasks. Between researching business acquisitions, managing my calendar, tracking networking events, and handling day-to-day operations, I was spending more time on busywork than on actual strategy.

So I built an AI assistant. His name is Crabby.

What Crabby Actually Does

Every morning at 7 AM, Crabby searches BizBuySell and LoopNet for businesses matching my criteria ($100K-$2M range, Orlando metro, no food service). I don't lift a finger.

At 8 AM, he delivers a briefing: weather, my calendar, follow-ups from yesterday, any urgent items. It's automatic.

He manages my Gmail—flagging important messages, responding to routine inquiries, keeping my inbox manageable.

He checks for networking events every Monday at 10 AM. I get a list of Chamber events, professional meetups, and opportunities that actually matter.

He books appointments, makes calls, researches competitors, and handles the stuff that used to eat my afternoons.

Here's what I've learned: ChatGPT won't do this out of the box. You need to:

• Build a memory system (I use daily logs + curated long-term memory files)
• Set up automation schedules (we use cron jobs for timed tasks)
• Connect your actual tools (Gmail, Calendar, browser automation, code execution)
• Give it clear instructions about your timezone, your preferences, how you communicate

I spent time upfront configuring Crabby. Now he runs autonomously. Most days I just read his morning briefing and reply to the things he flags.

The Real Result

I'm looking at businesses to acquire. Before Crabby, I'd spend hours manually searching. Now I review his curated list and follow up on what looks promising.

The difference isn't marginal. It's transformative.

What This Means for You

If you're running a business—or managing a team—you've got the same problem I had. Too much administrative work. Not enough time for strategy.

The good news: This is trainable. The system I've built for Crabby can be adapted to your specific workflows.

I help business owners and professionals set up their own AI assistants. The process typically takes a few days of intensive configuration, then you get your afternoons back.

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Evan Borenstein is the Principal at Highland Private Office, a Winter Park, FL-based private investment office focused on business acquisition and operational excellence through technology integration.