The Rentish Podcast

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We’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. 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.

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What 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 flow
• Why strong screening protects your properties long-term
• How clear expectations reduce landlord stress
• What experienced investors do differently from beginners

Ray's courses: 

• Real Estate Inner Circle
• Inner Circle Masterclass

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.

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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.

Follow us on Instagram 

Send us Fan Mail

In 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 

Send us Fan Mail

Pets 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 

Send us Fan Mail

This episode originally aired on November 17, 2025, and we’re resharing it for the new year, as many investors are re-evaluating their financing options and exploring different loan types for real estate.

Zach and Patrick sit down with Alex Bekeza, the most highly reviewed loan officer on BiggerPockets, to break down DSCR loans (Debt Service Coverage Ratio), how they work, and what investors need to know as they plan their next moves.

Whether you’re looking to scale your rental portfolio, explore BRRRR strategies, or understand financing options that rely on property performance instead of personal income, this conversation is packed with practical insights that still hold strong heading into 2026.

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 

Send us Fan Mail

With a new year underway, many aspiring investors are looking for the smartest way to break into real estate, and house hacking remains one of the most powerful ways to get started.

In this episode of The Rent-ish Podcast, we’re joined by Cincinnati-based developer John Blatchford to walk through how first-time investors can use house hacking, creative financing, and smart renovations to build equity from day one.

While this conversation was originally recorded on July 21, 2025, the strategies John shares are evergreen and especially relevant for anyone planning their first move into real estate this year.

We cover how to fund your first deal, what to look for in a property, and how to turn a single home into the foundation of a long-term investing strategy.

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 

Send us Fan Mail

With tax season approaching, understanding how real estate is taxed, and how to legally reduce what you owe is more important than ever.

In this episode of The Rent-ish Podcast, we’re joined by tax strategist KC Chohan to break down the foundational tax strategies every real estate investor should understand, whether you own one property or several.

While this conversation was originally recorded on September 29, 2025, the strategies discussed are evergreen concepts that continue to matter year after year, especially as investors prepare their taxes.

We cover the tax basics many investors overlook, common mistakes that cost people money, and how to think strategically about taxes before you buy your next property.

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 

Send us Fan Mail

In this episode of the Rent-ish Podcast, hosts Zach and Patrick welcome William Hollis, founder and CEO of Raise AI, to discuss the intersection of artificial intelligence and real estate investing. Hollis shares his journey from coding at a young age to realizing the inefficiencies in capital raising within the real estate sector. The conversation explores how AI can streamline processes, the emotional aspects of real estate transactions, and practical advice for first-time investors. Hollis emphasizes the importance of personal connections in residential real estate while also highlighting the potential for AI to revolutionize the industry.

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 

Send us Fan Mail

It’s a Christmas episode of The Rent-ish Podcast 🎄🏠

In this holiday special of Real Estate Reel, we break down the iconic Home Alone house, aka the McCallister Mansion, and what it would really be worth in today’s real estate market.

We cover:

• Where the real Home Alone house is located
• The current value of the McCallister house
• What could it rent for today
• Whether the family could realistically afford it in 1990
• How movie fame impacts home values

Blending Christmas nostalgia, real estate insights, and pop culture, this episode is perfect for fans of holiday movies, iconic homes, and property value breakdowns. Article to read more on this: 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