Jonathan Greene welcomes back Katie Cline, a senior global PR and communications leader turned hospitality and short-term rental expert, to explore her evolving philosophy behind Second Home First. Katie shares the personal story that led her to buy a vacation home before a primary residence—and how that unconventional decision unlocked both financial flexibility and deeper family experiences.

They discuss why renting in high-cost cities can coexist with smart real estate investing, how short-term rentals can function like a hybrid between lifestyle asset and retirement strategy, and why mindset—not money—is often the biggest barrier holding people back. Katie also explains how designing properties around personal preferences creates stronger guest experiences, better reviews, and more resilient performance across markets.

The key takeaway: real estate doesn't have to follow a single, traditional path. By aligning investments with lifestyle goals, hospitality values, and intentional design, investors can build assets that generate income today while still creating meaningful memories along the way.

• What "Second Home First" really means—and why it challenges the traditional homeownership timeline

• How short-term rentals can provide both lifestyle benefits and long-term financial security

• Why renting a primary home can offer flexibility while still building wealth through real estate

• The importance of designing properties around your own preferences and ideal guest avatar

• How hospitality mindset and intentional design drive better bookings and guest experiences

• Why breaking from conventional investing narratives can open up more creative opportunities

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Katie:

Website: http://buyyoursecondhomefirst.com/

Youtube: https://www.youtube.com/@SecondHomeFirst

Instagram: https://www.instagram.com/buyyoursecondhomefirst/

LinkedIn: https://www.linkedin.com/company/second-home-first/

Episode 216: https://zenandtheartofrealestateinvesting.com/podcast/216/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

Jonathan Greene sits down with Steph Weber, CEO of The Weber Co., to break down why short-term rental owners can't rely solely on Airbnb if they want long-term control and growth. Steph explains how direct branding protects your business from platform changes, helps guests connect emotionally to what you offer, and creates a clearer path to repeat stays and referrals.

They also dig into what it actually takes to build a brand guests remember, beyond pretty photos and a few amenities. Steph shares how to define a real target audience (often starting with yourself or a past/future version of yourself), how to turn amenities into guided experiences, and why collecting guest emails is one of the simplest, most overlooked moves STR operators can make.

The biggest takeaway: today's STR world isn't a side hobby—it's a hospitality business. And the operators who win are the ones who design intentionally, market consistently, and build a brand they own.

• Why direct branding matters when you don't control the platform that drives bookings

• How Airbnb changes can impact hosts—and why brand autonomy is the hedge

• What it means to create a "branded guest experience" (not just a place to sleep)

• How to define your avatar and design for a specific audience (not the masses)

• Why email lists are "low-hanging fruit" and how they power direct bookings

• Turning amenities into intentional rituals and guided experiences guests remember

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Steph:

Website: http://theweberco.com/

Instagram: http://instagram.com/theweberco

LinkedIn: https://www.linkedin.com/in/stephweberbrandcoach/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

Jonathan Greene sits down with Joe Rinderknecht, multifamily investor and co-founder of Cowboy Capital, to explore how he built a real estate portfolio by staying curious, solving problems, and building long-term relationships with owners. Joe shares how he broke into multifamily with seller financing, how he used subject-to strategies to help owners avoid foreclosure, and why empathy has become foundational to his investing style. Jonathan and Joe also explore the lessons learned from managing smaller properties, scaling into larger ones, and developing the operational discipline needed to create durable performance.

Throughout the conversation, Joe explains how he approached deal structure early in his career, the importance of understanding seller pain points, and how his "word is bond" philosophy continues to shape the way he raises capital and works with investors now. He also reflects on partnership dynamics, risk tolerance, and the evolution from doing everything yourself to delegating, documenting, and building systems that allow a team to grow.

Listeners will walk away with a grounded reminder that momentum in real estate often comes from doing the right thing—helping people, thinking long-term, and being willing to learn from every deal, no matter the size.

• How Joe got into multifamily through seller financing and why creative structures helped him get started without traditional barriers.

• The subject-to foreclosure story that shaped Joe's understanding of empathy, negotiation, and long-term relationship building.

• Why smaller properties became Joe's training ground for learning asset management, communication, and systems.

• How Joe's risk tolerance shifted over time and how partnership dynamics supported that growth.

• The importance of documentation, checklists, and processes as a business scales.

• Why Joe believes relationships—not deals—are the real foundation of a sustainable real estate career.

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Joe:

Website: https://cowboycapital.us/

Youtube: https://www.youtube.com/@cowboycapital.us2025

Facebook: http://facebook.com/joe.rinderknecht

Instagram: https://www.instagram.com/joe_rinder

LinkedIn: https://www.linkedin.com/in/joerinderknecht/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.