Episodes

  • 294: Capital Preservation and Resilient Returns Through Real Estate with Ari Rastegar

    294: Capital Preservation and Resilient Returns Through Real Estate with Ari Rastegar
    Nov 13 2025
    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene welcomes Ari Rastegar, founder and CEO of Rastegar Capital and author of The Gift of Failure. Ari shares his journey from delivering pizzas and attending law school to building a vertically integrated real estate platform with institutional-scale developments across the country. The conversation centers on discipline, philosophy, and how setbacks became the foundation for both his personal growth and business success. Jonathan and Ari explore the mindset behind enduring market "winters," the cyclical nature of real estate, and why failure is an essential teacher. Ari discusses his approach to entitlements and master-planned communities, his prediction for one of the largest real estate booms in decades, and how technology—from robotics to 3D printing—could reshape the cost and speed of new construction. He also opens up about health, daily habits, and the quiet discipline that sustains high performance in volatile times. Listeners will take away a deeper understanding of how to balance ambition with patience, why zoning and long-term planning are undervalued edges, and what it means to invest in projects—and people—with lasting value. Ari's story is a reminder that compounding growth begins not in markets, but in the consistency of who you are when no one's watching. In this episode, you will hear: How a $3,500 land purchase in law school launched Ari's development career during the run-up to the Great Financial Crisis Why he views market "winter seasons" and failures as essential to building a resilient, multi-billion-dollar real estate platform The demographic, technological, and housing-supply forces that he believes will drive an unprecedented real estate boom over the next decade How personal development, tiny daily improvements, and emotional awareness compound into better business decisions Why zoning, entitlements, and construction innovation (including 3D-printed and robot-built housing) are critical to solving the housing shortage How Rastegar Capital structures large projects so accredited investors can co-invest alongside major institutions Follow and Review 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. Supporting Resources Connect with Ari: Website: www.rastegarcapital.com Youtube: https://www.youtube.com/@rastegarcapital Facebook: https://www.facebook.com/rastegarcapital Instagram: https://www.instagram.com/rastegar/ LinkedIn: https://www.linkedin.com/company/rastegarcapital/ Twitter: https://x.com/arirastegar 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.
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    57 mins
  • 293: Real Estate Investments For the Alternative Investor with Scott Lurie

    293: Real Estate Investments For the Alternative Investor with Scott Lurie
    Nov 10 2025
    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by longtime Milwaukee investor and lender Scott Lurie. Scott is the founder and owner of F Street Investments and The Hard Money Co., with deep experience in flipping, multifamily, industrial, private equity, and property management. Together, they explore what it really takes to build durable real estate and lending businesses across multiple cycles, from early "We Buy Ugly Houses" days to large multifamily conversions and a nine-figure lending platform. Scott and Jonathan dig into why "local always wins" in real estate, how national wholesalers have damaged the reputation of the industry, and the way relationship-driven business still compounds over decades. Scott explains the economics behind converting older Residence Inn hotels into multifamily, how he thinks about replacement cost and basis, and why tax-incremental financing has been key to new development in southeastern Wisconsin. They also unpack the coming pain in overlevered Class A multifamily, the role banks will play, and how disciplined operators can navigate the next 18 months. Listeners will come away with a clearer picture of what to look for in both operators and lenders, how to think about downside protection, and why character and work ethic are still the real edge in real estate. Scott's stories from buying hundreds of units at the bottom of the Great Financial Crisis and bootstrapping his lending company offer a grounded blueprint for building something that lasts—without chasing Lamborghinis or social media fame. In this episode, you will hear: How Scott went from a zero-experience franchisee with "We Buy Ugly Houses" in 2003 to a seasoned operator with a nationwide portfolio Why he believes local investors still have a huge edge over virtual buyers and national wholesalers—and how those wholesaler models created reputational damage The business case for converting older Residence Inn hotels into apartments, and why understanding replacement cost and basis matters more than buzzwords Scott's view on overlevered Class A multifamily, rising interest rates, and the equity erosion he expects to see over the next 18 months How The Hard Money Co. underwrites borrowers (closing only 7–9% of applications) and the behaviors that separate consistently successful flippers from those who end up in foreclosure Lessons from scaling to hundreds of units and a nine-figure lending platform while keeping investors first and building a track record of on-time payments Follow and Review 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. Supporting Resources Connect with Scott Website: fstreet.com Youtube: https://www.youtube.com/@fstreet414 Facebook: https://www.facebook.com/fstreetinvest/ Instagram: https://www.instagram.com/fstreet_invest/ Website: thehardmoneyco.com 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.
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    54 mins
  • 292: Why Self Storage is a Recession-Resistant Industry with Joe Downs

    292: Why Self Storage is a Recession-Resistant Industry with Joe Downs
    Nov 6 2025

    Jonathan Greene sits down with self-storage investor and operator Joe Downs, CEO of Bellrose Storage Group, which sources, acquires, and manages self-storage facilities across the East and Southeast. With a background in commercial real estate, capital raising, and distressed second mortgages, Joe explains how he pivoted into self-storage after discovering just how mom-and-pop dominated and under-optimized the space really was.

    Their conversation explores why self-storage is still far from "too late," how technology and remote management have transformed operations, and why small, overlooked facilities under 30,000 square feet can be a goldmine for investors willing to modernize them. Joe also breaks down creative plays like boat and RV storage, industrial outdoor storage, and converting large vacant retail boxes into multi-revenue storage campuses.

    Listeners will come away with a grounded understanding of why self-storage is such a powerful niche, what to look for in a mom-and-pop facility, and how to avoid overpaying by underwriting expenses correctly. Joe and Jonathan also discuss the importance of relationships and "caretaker" mentality with long-time owners, the role of SBA loans, and how to keep shiny object syndrome in check while still recognizing adjacent opportunities.

    In this episode, you will hear:

    • How Joe went from distressed debt and 1031 capital raising to building a self-storage platform

    • Why self-storage is still largely mom-and-pop owned and what that means for opportunity

    • How technology, remote management, and autopay have transformed facility operations

    • What to look for in a first small storage acquisition and how to approach owners as a "caretaker"

    • The importance of underwriting real expenses (marketing, tech, management) so you don't overpay

    • Creative self-storage derivatives, including boat and RV storage, IOS, and big-box retail conversions


    Follow and Review
    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.

    Supporting Resources

    Connect with Joe Downs:

    Website: https://belrosegrp.com/

    Facebook: https://www.facebook.com/belrosestoragegroup

    Twitter: @downsjoe

    LinkedIn: https://www.linkedin.com/in/joe-downs-7990851/

    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.

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    53 mins
  • 291: The Overlooked Asset Class That Outperforms In Uncertain Markets with Tim Woodbridge

    291: The Overlooked Asset Class That Outperforms In Uncertain Markets with Tim Woodbridge
    Nov 3 2025

    In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Tim Woodbridge, co-founder of WCG Investments, to discuss how he transitioned from a healthcare career to building a portfolio of 19 mobile home parks across the Southeast. Tim shares the lessons he's learned about scaling through partnerships, managing risk with conservative underwriting, and improving communities through value-driven operations.


    The conversation explores his early challenges finding deals, developing trust with brokers and lenders, and learning how to take imperfect action without losing discipline. Tim explains why collaboration and follow-up matter as much as capital, what separates good due diligence from guesswork, and how his team builds sustainable systems to support investors and residents alike.


    This episode offers a grounded look at what it takes to grow in a niche asset class while maintaining long-term perspective, thoughtful leadership, and a genuine focus on people.

    In this episode, you will hear:

    • How partnerships built on complementary strengths lead to better deals
    • The importance of trust and transparency with brokers and lenders
    • Common due diligence pitfalls that can derail returns
    • Why realistic underwriting protects both operators and LPs
    • How consistent follow-up leads to unexpected opportunities
    • The role of community improvements in responsible investing

    Follow and Review
    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.

    Supporting Resources

    Connect with Tim Woodbridge

    Website: www.wcginvestments.com

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

    Facebook: https://www.facebook.com/wcginvestments

    Instagram: https://www.instagram.com/tim.woodbridge/

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

    E-Book - https://wcginvestments.cashflowportal.com/leads/e-book

    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.

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    48 mins
  • 290: Why Accurate Financials Lead To Better Decisions and More Profit with Max Emory

    290: Why Accurate Financials Lead To Better Decisions and More Profit with Max Emory
    Oct 30 2025

    Jonathan welcomes Max Emory, founder of Time Capital Bookkeeping & CFO Solutions, a bookkeeping educator and active investor. Together, they explore why clean books form the foundation of every real estate business and how accurate categorization impacts both taxes and lending. Max explains what decision-ready financials allow investors to do, including timing acquisitions, managing cash flow, and avoiding costly tax surprises. He also shares why onboarding with a professional bookkeeper is intensive but worthwhile, how your bookkeeper, CPA, and attorney should collaborate, and the most common financial pitfalls he corrects for flippers, wholesalers, and landlords.

    Max shares his path from serving in the Marine Corps to purchasing his first duplex in Columbia, South Carolina, and scaling through clustered small multifamily properties using the BRRRR strategy. He discusses early challenges such as hiring and firing property managers, building a technology-driven team, and using neighborhood comps and appraisals to improve accuracy. He explains how commingling funds can disrupt operations and increase bookkeeping costs, how simple categorization mistakes can inflate taxable income by thousands, and how to adjust profit and loss reporting to support specific goals, whether maximizing lendability or minimizing taxes.

    Listeners will leave with a clear checklist for preparing to hire a professional bookkeeper, an understanding of which financial metrics matter most, and the confidence to treat bookkeeping as a strategic advantage rather than a yearly obligation.

    In this episode, you will hear:

    • Why bookkeeping is the financial foundation—and how it drives tax strategy, lending, and acquisitions

    • The most expensive mistakes Max sees (miscategorization, commingling, missing capex visibility)

    • How to align your bookkeeper, CPA, and attorney so your entity structure helps operations

    • A simple starter system for receipts, statements, and deal docs (even before you hire help)

    • When and why to keep taxable income high (and when to compress it)

    Follow and Review

    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.

    Supporting Resources

    Connect with Max Emory

    Website: https://www.timecapitalbcs.com/

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

    Facebook: https://www.facebook.com/themaxemory

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

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

    Tik Tok: https://www.tiktok.com/@timecapitalbcs0?lang=en

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

    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
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    52 mins
  • 289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells

    289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells
    Oct 27 2025

    On this week's episode, Jonathan welcomes Jon Wells, a real estate matchmaker, syndicator, and longtime realtor with A Better Way Realty and managing partner at Alpha Network—for a candid look at what actually builds durable wealth. Jon traces his journey from early "fix-and-flips" to higher-conviction "fix-and-holds," and ultimately to group homes leased on commercial-style terms. He explains why patience, operator quality, and underwriting discipline matter more than shiny objects, and how aligning with the right partners turns headaches into hands-off income.

    As the conversation unfolds, they unpack contractor pitfalls, slim-margin flips that turn into flops and the relief of triple-net-style leases where the business, not the landlord, handles the day-to-day. Jon shares why he prefers renting large, lightly modified homes to sober-living/mental-health operators (versus carving up houses), why meeting new operators is the hardest part of this niche, and how option agreements can create shared upside. They also dive into passive vs. active choices, due-diligence checklists for syndications, and the value of investing in what you truly understand.

    Listeners will come away with a calmer, longer-term lens: start with who you trust, de-risk with questions that reveal how an operator thinks, and don't mistake speed for progress—especially when cash flow and sleep-at-night returns are the goal.

    In this episode, you will hear:

    • Why slim margins turn flips into long, stressful holds—and how to avoid it.

    • The group-home model Jon uses: bigger homes, egress and safety upgrades, and commercial-style leases to vetted operators.

    • Triple-net thinking for residential assets: fewer calls, clearer responsibility, steadier income.

    • Trust and due diligence: the questions that de-risk syndications and funds—and when "no answer" means "no deal."

    • Why investing in what you actually know (and who you truly trust) beats chasing neon "opportunities."

    • How to choose between passive and active plays based on temperament, skills, and season of life.

    Follow and Review

    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.

    Supporting Resources

    Connect with Jon Wells

    Website - www.abetterwayrealty.comFacebook - https://www.facebook.com/jonwells69Instagram - https://www.instagram.com/jonwells5280/Linkedin - https://www.linkedin.com/in/jonwellsrealtor/

    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
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    49 mins
  • 288: Building a Capital Gains Tax Exit Plan with Brett Swarts

    288: Building a Capital Gains Tax Exit Plan with Brett Swarts
    Oct 23 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Brett Swarts, founder of Capital Gains Tax Solutions, to explore strategies for minimizing capital gains taxes when selling real estate or business assets. Brett Swarts is the founder of Capital Gains Tax Solutions, specializing in advanced strategies to help investors defer or eliminate capital gains taxes. With extensive experience in structuring Deferred Sales Trusts and other exit strategies, Brett has guided numerous real estate and business owners in building tax-efficient, long-term wealth plans. Brett explains how the Deferred Sales Trust (DST) offers a flexible alternative to traditional 1031 exchanges, providing investors with greater control over timing, liquidity, and investment choices while deferring taxes in a manner that is legally compliant under IRS guidelines. Brett outlines the mechanics of a DST, detailing how proceeds from a sale can be structured to defer capital gains taxes and reinvest in a variety of assets. You'll get insight into the advantages of a DST over standard tax-deferral methods, including reduced pressure to time the market, expanded diversification opportunities, and the ability to preserve wealth across multiple investment vehicles. Jonathan and Brett also discuss common misconceptions about tax-deferred strategies, emphasizing the importance of understanding legal structures and working with experienced professionals. The conversation highlights how these tools can fit into a broader estate and legacy planning framework, ensuring that wealth is transferred efficiently to future generations while maintaining flexibility for investors today. Several real-world examples demonstrate how investors have effectively utilized DSTs to manage risk, maintain cash flow, and safeguard portfolio value in dynamic markets. Brett emphasizes that while a DST can benefit many investors, it is particularly effective for those with significant gains, complex portfolios, or long-term wealth preservation goals. The discussion concludes with actionable guidance on evaluating whether a DST aligns with an investor's exit strategy and long-term financial objectives. By the end of this episode, you'll understand how to approach capital gains tax planning strategically, integrating DSTs into their broader real estate and business investment strategies. Jonathan and Brett provide a clear framework for deferring taxes, diversifying holdings, and protecting wealth, enabling investors to make informed decisions that align with both their financial and personal objectives. In this episode, you will hear: How the Deferred Sales Trust works as an alternative to 1031 exchanges Ways to defer capital gains taxes while maintaining investment flexibility Strategies for diversifying proceeds and protecting portfolio value Common misconceptions about tax-deferred exit strategies How estate and legacy planning can integrate with a DST Follow and Review: We'd love for you to follow us if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: Capital Gains Tax Solutions website - www.capitalgainstaxsolutions.com Build It To Billions on YouTube - www.youtube.com/@BuildItToBillions Brett Swarts on Facebook - www.facebook.com/brett.swarts Brett's Instagram - instagram.com/brett_swarts Connect with Brett on LinkedIn - www.linkedin.com/in/brett-swarts Website - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties TikTok - www.tiktok.com/@trustgreene Zillow - www.zillow.com/profile/StreamlinedReal Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/streamlinedproperties Email - info@streamlined.properties Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
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    47 mins
  • 287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte

    287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte
    Oct 20 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Luis Belmonte, a lifelong real estate investor, to explore the lessons he's learned over decades of investing in multifamily, industrial, and commercial real estate across the U.S. and internationally. Luis shares his early experiences, including navigating the complexities of San Francisco's real estate market in the pre-MLS era, identifying overlooked investment opportunities, and managing properties during challenging economic cycles. His stories reveal how creativity, persistence, and relationship-building have been central to his long-term success. Luis takes us back to his first multifamily acquisitions, explaining the strategies he used to uncover deals when information was scarce. From attending broker meetings with nothing but a notebook and a case of beer to identifying opportunities through obituaries, Luis emphasizes the importance of proactive deal sourcing and building relationships with those who have local knowledge. He also discusses the transformative effect of San Francisco rent control, illustrating how strategic management and patience can yield extraordinary returns over time. The conversation then shifts to international real estate development, highlighting the stark contrasts between regulations and construction practices in countries like Mexico and Japan compared to the United States. Luis recounts overcoming challenges such as unclear land ownership, lack of infrastructure, and differing bidding practices, underscoring the value of understanding local systems and collaborating with trusted partners. Whether navigating city politics in San Francisco or creating operational solutions abroad, Luis demonstrates that preparation and local expertise dramatically reduce risk and unnecessary costs. Jonathan and Luis also examine the current economic landscape, including interest rates and cyclical market patterns. Luis offers perspective on borrowing, refinancing, and interest rate history, reinforcing that measured and disciplined investing remains key, regardless of market fluctuations. Finally, Luis shares his preferred asset classes for long-term wealth creation: multifamily and warehouse properties. He emphasizes the importance of choosing an investment style aligned with one's personality, seeking downside protection, and understanding operational realities to maximize returns. You'll come away with practical advice on building sustainable real estate wealth, managing risk, partnering effectively, and identifying investment opportunities that others might overlook. Luis's guidance is grounded in decades of real-world experience, making this episode essential for both new and seasoned investors looking to grow their portfolios with confidence. In this episode, you will hear: How Luis sourced early San Francisco deals before online MLS existed Creative approaches to finding undervalued properties and motivated sellers The impact of rent control on long-term investment returns Lessons from international real estate development in Mexico and Japan Strategies for partnering, reducing risk, and avoiding "stupid taxes" Luis' preferred asset classes for consistent long-term wealth How interest rate cycles affect real estate investing and financing Follow and Review: We'd love for you to follow us if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: Seven Hills Properties website - 7hp.com Website - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties TikTok - www.tiktok.com/@trustgreene Zillow - www.zillow.com/profile/StreamlinedReal Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/streamlinedproperties Email - info@streamlined.properties Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
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    52 mins