S3, Podcast 1: Where AI Is Actually Working in Multifamily

AI isn't shrinking your job. Jacob Carter makes the case for why it's shifting it instead.

In this episode, Mike Brewer sits down with Jacob Carter, author of the new book “AI in Property Management,” who has spent his career building AI-first software for the multifamily industry. Jacob breaks down automation, conversational AI, generative AI, and agentic AI in plain terms, and makes the case that AI isn’t shrinking operator jobs. It’s shifting them.

Because the operators who get ahead of that shift will have the advantage. The ones waiting for it to settle down won’t.

Timestamps:

0:01 — Why most of the industry still thinks AI just means a chatbot

1:01 — Mike introduces Jacob Carter and his new book

2:08 — Where the idea for the book actually came from

4:11 — What actually counts as AI solving a problem, versus a shiny feature

5:47 — Where AI is producing the strongest outcomes in multifamily right now

6:44 — Is Jacob’s own company AI-first from the inside out

8:16 — Untangling automation, conversational AI, generative AI, and agentic AI

10:10 — The pyramid model for understanding every AI buzzword at once

10:40 — Agent-to-agent commerce, and how far away that moment really is

12:11 — Where humans need to stay in the loop, and where they shouldn’t

13:05 — The “new on-site team” and what AI absorbs first

15:08 — Humans, efficiency, and the shrinking human-in-the-loop spectrum

16:41 — On-site teams becoming community ambassadors instead of task-doers

17:58 — The data mess multifamily built over the last ten years

18:57 — Why chasing one clean source of truth is the wrong goal now

19:57 — The orchestration layer, and why “context is king” for the next 12 months

23:21 — The biggest misunderstanding about AI in multifamily right now

25:11 — Advice for owners, operators, and regional managers trying to cut through the noise

29:44 — The honest “I don’t know” answer on where AI goes next

32:10 — The two things Jacob wants every operator to walk away with

---

Jacob spent years building software for this industry before he spent a year writing about it, and the book’s argument is simpler than the buzzwords floating around it. AI in multifamily isn’t one thing. It’s a ladder, from broad machine learning down to the specific agentic tools doing work on the ground, and most operators are stuck thinking about the bottom rung.

This newsletter goes further than the episode has room for. It takes Jacob’s argument about the industry’s data mess and walks through what actually breaks when disconnected systems get an AI tool bolted on top of them, and what has to change first.

Read it here ⬇️