Zen and the Art of Real Estate Investing (2025)

04/09/2025

Repositioning Shopping Centers in Hometown Markets with Andy Weiner

Episode 274 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/274/

Shopping centers may not dominate headlines like multifamily or industrial, but they remain one of the most overlooked opportunities in commercial real estate.

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Andy Weiner, founder and president of RockStep Capital, to discuss how shopping centers, especially in hometown markets, continue to thrive. Andy shares his unique approach to repositioning retail properties, building coalitions with local leaders, and investing where others often overlook.

With decades of experience in retail and real estate, Andy has witnessed firsthand how Amazon, shifting consumer habits, and COVID have transformed the shopping center landscape. Instead of retreating, he’s leaned into markets with essential drivers—universities, military bases, strong hospital systems, and tourism—that support community retail. His RockStep coalition model brings together local investors, banks, and municipalities to revitalize shopping centers, creating not just strong investments but also community anchors.

Jonathan and Andy explore the nuances of evaluating tenants, identifying markets with sustainable growth, and managing assets in a way that prioritizes both profitability and long-term community impact. This conversation challenges the narrative that retail is dead, highlighting why shopping centers in secondary and tertiary markets may be some of the most compelling opportunities available today.

01/09/2025

Why An ESPN SportsCenter Anchor Is Knee-Deep in Real Estate with Gary Striewski

Episode 273 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/273/

What happens when a SportsCenter anchor trades in highlight reels for house hacking?

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes ESPN’s Gary Striewski to share his story of becoming a DIY real estate investor while holding down a demanding broadcasting career. Gary takes listeners inside his approach to building wealth, one property at a time, without falling into the “guru culture” that dominates so much of real estate social media.

Gary’s journey began with his first home purchase in 2018, following his move to ESPN, which later paved the way for house hacking, renovations, and rental strategies. Today, he balances a full-time media career with managing a growing portfolio of long-term, short-term, and mid-term rentals across Connecticut and New Hampshire. His story is one of perseverance, adaptability, and treating tenants like partners rather than numbers.

From his early days of renovating while living without plumbing, to buying properties straight off the MLS, to learning the power of patience in real estate, Gary demonstrates how an intentional, human-centered approach can turn steady progress into a lasting portfolio. He and Jonathan also dive into the myths of instant wealth, why real estate should be viewed as a long game, and how personal discipline and flexibility create the foundation for success.

Tune in to hear how Gary Striewski proves that balancing a full-time career with intentional real estate investing is not only possible but deeply rewarding.

31/08/2025

This week on Zen and the Art of Real Estate Investing

New episode drops:

Ep. 273 - Why An ESPN SportsCenter Anchor Is Knee-Deep in Real Estate with Gary Striewski

Ep. 274 - Repositioning Shopping Centers in Hometown Markets with Andy Weiner

28/08/2025

Unlocking Your Legacy With Turn-Key Real Estate with Lindsay Davis

Episode 272 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/272/

In today’s episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Lindsay Davis, CEO of Spartan Invest to explore the world of turn-key real estate. Lindsay shares her journey from college landlord to building one of the leading turn-key investment companies in the Southeast. Their discussion covers the advantages of passive investing, the realities of property management, and how Spartan’s approach makes real estate accessible for investors nationwide.

Lindsay began her investing journey as a college student in Alabama, renting rooms to reduce tuition costs. After a rocky start as a landlord and a stint in corporate America, she shifted to flipping houses before finding stability and scale in rental properties. This led her to co-found Spartan Invest, a full-service turn-key provider offering single-family homes in Alabama, Tennessee, and Georgia.

For investors hesitant about the headaches of being a landlord, Lindsay explains how Spartan handles property acquisition, renovation, tenant placement, and ongoing management. By focusing on durability, affordability, and transparency, Spartan delivers rental properties designed for long-term performance and reduced maintenance.

Jonathan and Lindsay also discuss the profile of today’s turn-key investors, from W-2 employees seeking diversification to high earners priced out of their own markets. They cover the importance of choosing landlord-friendly states, understanding pro forma numbers, and staying engaged with your property manager. With entry points averaging around $165,000 and financing options that include competitive rates, Spartan opens the door to investors ready to grow their portfolios without the grind of flipping or self-management.

If you’ve ever wondered how to build a real estate legacy with minimal stress, this episode provides a clear look at how turn-key investing works and why it’s an attractive strategy in today’s housing market.

25/08/2025

Creating Netgains Through Property Management with Derek D Morton

Episode 271 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/271/

Property management may not be flashy, but it’s essential to successful real estate investing.
In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Derek Morton, founder and owner-broker of Netgain Property Management in Utah. Since 2016, Derek has built his company around balancing landlords’ expectations with tenants’ needs. With over 14 years of real estate experience, he shares stories, lessons, and practical strategies that show why effective property management is about more than just collecting rent.

Derek explains that many landlords underestimate what it takes to own rental property. Too often, investors assume hiring a property manager means they can step away entirely. Instead, he stresses the importance of staying engaged and managing the manager. He discusses how becoming more selective with clients improved both his business and his quality of life, and why setting expectations early with both tenants and owners prevents conflict later.

Technology is central to Derek’s approach. From maintenance platforms to financial reporting tools, automation helps his team streamline processes and reduce repetitive tasks. This frees up time for meaningful conversations and allows them to “people better” when human connection really matters. With these systems in place,

Derek has scaled his business across Utah while maintaining a strong focus on service.
Jonathan and Derek also touch on the realities landlords rarely anticipate—emergency repairs, tenant job loss, and unexpected life events. Derek highlights the importance of financial reserves and has redesigned his onboarding process to include an owner’s manual, welcome box, and annual reviews. These steps educate landlords and align expectations from the start, reducing long-term issues.

Looking ahead, Derek sees rental payments shifting to match how tenants manage money. Flexible or weekly payment options, along with security deposit alternatives, are becoming more common. He believes these changes reflect economic realities and can ease pressure on tenants while ensuring landlords get paid.

Jonathan underscores that property management isn’t a set-it-and-forget-it function. Investors who hire managers still need to stay involved, ask questions, and build trust. Derek’s philosophy of preparation, transparency, and accountability shows how effective property management strengthens portfolios, reduces stress, and creates long-term net gains.

Whether you’re new to rentals or scaling a portfolio, this episode highlights the systems and mindset that turn property management into a true asset for long-term success.

24/08/2025

Next week on Zen and the Art of Real Estate Investing

New episode releases:

Ep. 271 - Creating Net Gains Through Property Management with Derek D Morton

Ep. 272 - Unlocking Your Legacy With Turn-Key Real Estate with Lindsay Davis

Recording with:

Jon Wells

21/08/2025

The Ins and Outs of Real Estate Fund Administration with Mike Zane

Episode 270 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/270/

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Mike Zane, a real estate fund administrator at Lexcraft Advisors who specializes in supporting fund managers through the complexities of launching, managing, and scaling investment funds. With a background in accounting and years of experience working inside and alongside real estate funds, Mike offers a clear look at how fund administration works and why it’s critical to an investor’s long-term success.

Mike explains that many investors underestimate the operational and compliance demands of running a fund. From regulatory filings and investor communication to accurate financial reporting, fund administration is more than bookkeeping. It’s a system that keeps funds running smoothly and legally. He and Jonathan discuss the differences between starting a fund as a new manager versus transitioning from syndications, the importance of building strong investor relationships through transparency, and the role of a fund administrator in protecting both the manager and the investors.

They also cover why newer managers often underestimate the time and resources needed to manage a fund, how to streamline back-office operations without sacrificing accuracy, and the potential pitfalls of trying to handle everything yourself. Mike shares advice for setting up a fund correctly from the start, including knowing when to bring in outside help, the technology tools that make administration more efficient, and how proactive reporting can boost investor confidence.

For anyone considering starting a real estate fund or enhancing the one they already manage, this episode breaks down the process into manageable parts. It highlights the support systems that make the difference between chaos and control.

18/08/2025

How To Start Living Off Rentals with Kirby Atwell

Episode 269 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/269/

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Kirby Atwell, an Army veteran, real estate investor, and host of the Living Off Rentals podcast. Kirby’s journey from military service to financial freedom offers a practical roadmap for investors seeking a sustainable, high-cash-flow strategy.

Kirby’s interest in real estate began in 2006 while stationed in El Paso, Texas, after reading “Rich Dad Poor Dad.” His first purchase, a turnkey property across the street, sparked a career that would include multiple rental acquisitions before leaving the Army in 2011. Initially, Kirby built a high-volume house-flipping business, completing around 75 projects in five years. While the operation looked successful from the outside, the overhead, contractor management, and constant pressure to “feed the machine” made it an unsustainable treadmill.

Recognizing that his initial goal was freedom, not endless hustle, Kirby pivoted. After a short return to corporate work, he began acquiring long-term rentals in Northwest Indiana. A chance experiment, turning a basement apartment into an Airbnb, netted $22,000 in one summer, far exceeding the annual income from some of his long-term units. This discovery led him to transition entirely to short-term rentals, focusing on modestly priced multi-unit properties that could also work as long-term rentals if needed.

Kirby now manages 39 short-term rental listings, primarily clustered near Michigan City and Valparaiso, Indiana, with additional properties in southwest Florida. By concentrating on one region before expanding, he built economies of scale in operations, supply management, and cleaning services. His strategy centers on risk-averse investing—buying affordable properties in areas with steady demand drivers, from national parks to local universities—while maintaining the flexibility to pivot between rental strategies.

Jonathan and Kirby discuss the power of “reps” in real estate, why clustering investments boosts efficiency, and how to vet short-term rental opportunities by analyzing local competition. Kirby also shares his process for furnishing units cost-effectively, his rule of thumb for net returns (1% of purchase price monthly), and the importance of avoiding over-leverage.

Today, through his Living Off Rentals platform, Kirby coaches other investors to build similar portfolios. His philosophy combines conservative acquisition criteria with creative income strategies, allowing investors to create both cash flow and long-term equity without the burnout of high-volume flipping.

17/08/2025

Next week on Zen and the Art of Real Estate Investing

New episode drops:

Ep. 269 - How To Start Living Off Rentals with Kirby Atwell

Ep. 270 - The Ins and Outs of Real Estate Fund Administration with Mike Zane

Recording with:

Brett Swarts

17/08/2025

SAVE THE DATE

WED - SEPTEMBER 3RD - 6 TO 8 PM

Zen and the Art of Real Estate Investing In-Person Meetup

Location: Veggie Heaven, 473 Cedar Lane, Teaneck

Sponsor: Molson Law Firm, LLC

RSVP: https://bit.ly/rsvpzen

These are networking events. No pitching is allowed. We are here to build relationships and discuss real estate investin

14/08/2025

Designing and Operating a Boutique Wellness Resort with Diana Ossa and Josh Dobken

Episode 268 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/268/

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Diana Ossa and Josh Dobken to discuss the creation of their boutique wellness resort in Palm Springs. As a couple with a shared vision for conscious living, they transformed their dream into a real estate venture focused on wellness, sustainability, and community.

Diana and Josh talk about their approach to design and development, why they chose Palm Springs, and how they’re creating a guest experience that’s intimate, personalized, and grounded in nature. Their project isn’t just about hospitality. It’s about building something that reflects their values and lifestyle.

Jonathan explores how they approached the design process, from layout to material selection, and how they balanced the creative aspects with logistical and financial realities. They also discuss the importance of timing, trusting their instincts, and building a brand that speaks to a like-minded audience. Their story offers a firsthand look at how intentional living and real estate investment can align.

This episode is an honest and inspiring look at what it takes to create a boutique experience that blends business with purpose.

11/08/2025

Investing in Real Estate From a Position of Strength with Scott Trench

Episode 267 of Zen and the Art of Real Estate Investing is out everywhere you listen to podcasts!

Listen → https://zenandtheartofrealestateinvesting.com/podcast/267/

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Scott Trench, former CEO of BiggerPockets, co-host of the BiggerPockets Money podcast, and author of “Set for Life.” Their conversation dives into how Scott achieved financial independence through real estate and frugality, and how new investors can build the confidence and skills to invest from a position of strength.

Scott shares how his own path began with house hacking and strict expense management while working as a financial analyst. These early habits laid the foundation for his first duplex purchase and ultimately his real estate success. He explains that the core pursuit behind investing for most people isn’t financial wealth. It’s time freedom. Real estate offers one of the most accessible paths to achieve that, especially for everyday Americans with median incomes.

The conversation highlights the importance of personal accountability and developing an in-person community. While online education has its place, Scott emphasizes the lasting value of learning from real people, joining masterminds, and taking action on knowledge, not just theory. He also explains how engaging directly with tenants, even when difficult, builds the playbook necessary for long-term success.

Jonathan and Scott discuss why now might actually be an excellent time to buy, especially in smaller multifamily sectors. While high interest rates have sidelined many investors, price adjustments in certain markets have created new windows of opportunity. Scott reflects on his experience with both direct ownership and passive investing in syndications, candidly sharing why he prefers the control and reliability of local real estate over national trends.

They also touch on the FIRE (Financial Independence, Retire Early) movement and what early retirement actually means. For Scott, financial freedom isn’t about never working again. It’s about creating more choices. He encourages listeners to ignore the noise, avoid overpriced guru programs, and focus instead on sustainable investing strategies that fit their lives.

Throughout the episode, Scott keeps the advice actionable. He urges new investors to think critically, avoid fads, and build a strong foundation through frugality, education, and reps in the field. Whether you’re house hacking, looking at syndications, or considering commercial opportunities, the key is to approach each decision with discipline and awareness. The ultimate goal? Gaining control over your time, finances, and future.

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