The Rentish Podcast

Mid-Term Rentals EXPOSED: When They Win, When They Fail

Send us Fan MailWe’ve talked about long-term rentals. We’ve talked about Airbnb.But we’ve never talked about this.In this episode of The Rent-ish Podcast, Zach and Patrick welcome Bailey Kramer, the first guest we’ve ever had, to break down mid-term rentals, the in-between strategy most investors either misunderstand or completely ignore.Bailey shares how he started investing while still in college, why he chose mid-term rentals over traditional leasing, and what actually makes this strategy work (and fail). We get into the real numbers, why furnishing matters more than people expect, how tenant screening changes by platform, and why mid-term rentals are not the “safe middle ground” everyone assumes.If you’ve ever wondered whether mid-term rentals are a hidden opportunity or a risky distraction, this episode gives you the honest answer.No hype. No gurus. Just the reality.Check out Bailey's YouTube channel, where he has a plethora of real estate information and tips. HEREhttps://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.Follow us on Instagram 

Why the Best Landlords Treat Tenants Like Customers

Send us Fan MailWhat separates landlords who constantly deal with headaches from those who build stable, profitable portfolios?In this episode of The Rent-ish Podcast, Zach and Patrick sit down with Ray Glymph, a real estate investor with over 100 doors, to break down one of the most overlooked success drivers in real estate: how you treat your tenants.Ray explains why treating tenants like customers leads to better retention, fewer evictions, lower turnover, and why lowering rent is often smarter than lowering standards. He walks through practical tenant-screening principles, communication strategies that prevent problems before they start, and lessons learned from managing dozens of units at scale.You’ll also hear Ray’s approach to fix-and-flip investing, why “ugly” properties can be the most profitable, and how mentorship accelerated his growth as an investor.If you’re a new or growing landlord looking for practical, real-world education, not hype, this episode breaks down what actually works.You’ll learn:How tenant treatment directly impacts cash flowWhy strong screening protects your properties long-termHow clear expectations reduce landlord stressWhat experienced investors do differently from beginnersRay's courses: Real Estate Inner CircleInner Circle Masterclasshttps://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.Follow us on Instagram 

Why the Investors Winning Quietly Are Using AI

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 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.Follow us on Instagram 

House Flipping vs Renting: Which Strategy Builds More Wealth in Real Estate Investing?

Send us Fan MailIn this episode of the Rent-ish Podcast, hosts Zach and Patrick are excited to welcome Mackaylee, a powerhouse in the Kansas City real estate space as an agent, investor, and house flipper with over 10 years of experience. Over the past four years alone, she’s flipped more than 300 units, generating over $45 million in revenue.In addition to flipping, Mackaylee currently self-manages around 50 rental units, which bring in roughly $80,000 in monthly rent. She’s also actively overseeing multiple rehab projects at any given time, giving her a hands-on perspective across every side of real estate investing.In this episode, Mackaylee shares her journey into real estate, what it’s really like managing rental properties, and why consistency (and creativity) are essential to long-term success, especially in house flipping. She also breaks down what she’s seeing in the Kansas City rental market, why rental demand is so strong, and the key factors investors should consider when evaluating a property, including curb appeal, market dynamics, and deal strategy.Whether you’re trying to decide between flipping vs renting, learning how to analyze investment properties, or looking for real-world advice on getting started in real estate investing, this episode is packed with practical takeaways you can apply immediately.Check out Mackaylee on her website HERE!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.Follow us on Instagram 

Pets, Policies, and Fair Housing: What Landlords Need to Know

Send us Fan MailPets are part of the rental equation, whether landlords like it or not. In this episode, hosts Zach and Patrick sit down with Victoria Cowart, VP of Education at PetScreening, to break down what landlords actually need to know about pets, assistance animals, and fair housing compliance.Victoria shares her path into property management and why education is the foundation of smart rental decisions. The conversation covers the real impact pets have on rentals, common mistakes landlords make with pet policies, and the critical differences between pets and assistance animals. If you’re navigating pet ownership in your rentals (or trying to avoid legal headaches), this episode delivers practical, landlord-friendly guidance you can use right away.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.Follow us on Instagram