Why the Investors Winning Quietly Are Using AI

2026-02-09

Download

Send us Fan MailThis episode was originally released on December 29, 2025. We’re resurfacing it because, heading into the new year, something has become clear: AI isn’t coming to real estate — it’s already here, and it’s quietly separating operators.In this episode of The Rent-ish Podcast, Zach and Patrick sit down with William Hollis, founder and CEO of Raise AI, to talk about how artificial intelligence is reshaping real estate investing in ways most people aren’t noticing yet.This isn’t an AI...

Send us Fan Mail

This episode was originally released on December 29, 2025. We’re resurfacing it because, heading into the new year, something has become clear: AI isn’t coming to real estate — it’s already here, and it’s quietly separating operators.

In this episode of The Rent-ish Podcast, Zach and Patrick sit down with William Hollis, founder and CEO of Raise AI, to talk about how artificial intelligence is reshaping real estate investing in ways most people aren’t noticing yet.

This isn’t an AI hype conversation. It’s about leverage.

William breaks down how AI is being used behind the scenes to improve underwriting speed, reduce capital friction, sharpen decision-making, and help serious investors operate more efficiently, without replacing human judgment.

They also discuss why house hacking remains one of the strongest entry points into investing, the emotional realities of residential real estate, and why investors who dismiss AI as “future tech” may already be falling behind.

If you own multiple units and care about scale, efficiency, and staying competitive over the next cycle, this conversation is worth your time.

Listen to the full episode and others here: linktr.ee/rentishpod

https://ledgre.ai/?utm_source=Podcast&utm_medium=OrganicSocialMedia&utm_campaign=Feb2026Promotion

Learn More https://innago.com/podcast/

https://joincohorts.com/

Sponsors:

Innago is a free, online property management software designed for landlords, particularly those managing small to medium-sized portfolios. It offers a range of features to simplify tasks like rent collection, lease management, maintenance requests, and tenant screening.

Ledgre is an All-in-One Accounting Software Built for Rentals. Organize property transactions, track expenses, and automate rental accounting with simple software focused on your industry.

Cohorts where serious real estate leaders level up. Join a curated peer group of founders, principals, and GPs who meet monthly in small, high-value circles. No fluff—just real insights, real accountability, and direct access to people who’ve done it before.

Comments (3)