Ep 47 | Why AI for PM Feels So... Meh

If you’ve ever clicked “Assistant” and ended up back in a form… this episode is for you.

In this episode, Pablo Gonzalez breaks down why most “AI-powered” tools still make you do the work. He explains why so many AI tools feel off when it gets bolted onto a ship built for a different ocean.

Drawing from a viral LinkedIn post (which wasn't written about property management but might as well have been) and a brutally honest conversation with Kyle Erb, Director of Systems at Real Property Management (and someone who's lived through the shift), Pablo pulls back the curtain on:

🚫Why AI features from legacy SaaS tools fall flat
🚢 The “Wrong Ship Problem”: What happens when the destination changes, but your team, tools, and culture don’t
🤖 Why injecting AI into old systems breaks faster than it helps (and how agentic AI flips the script)
🧠 The difference between automation for efficiency vs. AI built to own outcomes

If AI has felt “meh,” maybe you haven’t seen the right AI, or the right team building it. This episode is your wake-up call to stop settling for dashboards and start building with vision.

🎧 Listen now and step aboard the AI-first ship.

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Chapters:

00:00 The AI “Meh” Problem in Property Management
01:12 Why Incumbent SaaS Can't Do Real AI
02:48 The Wrong Ship Analogy
04:14 Kyle Herb’s Insight: Why AI Agents Break Forms
05:50 The Culture Clash: Outcome Ownership vs. Scale Obsession
07:36 A Personal Story of Mismatched Scaling
09:00 The Influence Trap: Who’s Shaping Your AI Beliefs?
10:54 The First AI-First Voice Who Gets It - Kyle Herb
12:00 Closing Invitation: Build the AI-First Ship With Us