This episode of Real Deal Investing features hosts Larry Mastropieri, Jerron Kelley, and Griffin Wallace interviewing Armand Grossman—a highly experienced entrepreneur, educator, and real estate investor with a fascinating, unconventional life story.

Armand begins by recounting how his early path toward becoming a lawyer was interrupted by the Vietnam draft. Instead of entering law, he became a teacher, which ultimately reshaped his career trajectory. His time as a high school guidance counselor and basketball coach in Miami’s Liberty City during school desegregation proved transformative. There, he implemented forward-thinking concepts like goal-setting and visualization—techniques that contributed to his team’s remarkable success and foreshadowed his later work in personal development.

He then shares his first entrepreneurial ventures, including forming and selling shares in a semi-pro football team, which gave him early exposure to business structuring and capital raising. From there, Armand transitioned into real estate, crediting mentorship as a pivotal factor. He highlights creative strategies like lease options that allowed him to acquire property without traditional financing—an approach he later taught to thousands.

A major theme throughout the conversation is mindset. Armand emphasizes the power of belief, warning against “the thief in your head”—self-doubt that prevents people from achieving success. He shares how personal development content (like Earl Nightingale recordings) transformed his approach to teaching and business, leading him into a long career in real estate education and seminars.

The discussion also dives into advanced investment strategies, particularly single-tenant triple net (NNN) leases. Armand explains their appeal: predictable income, minimal landlord responsibilities, and corporate-backed leases. He contrasts this with the challenges of managing residential tenants, reinforcing why many investors transition to more passive models over time.

Additionally, he discusses seller financing as a powerful wealth-building and tax-deferral strategy, and reflects on his decades in education, where he mentored students who later became highly successful entrepreneurs and real estate investors.

Armand’s upcoming book, The Privilege of Adversity, encapsulates his philosophy that hardship is often the foundation of success. He reinforces that failure, struggle, and persistence are essential ingredients in achieving long-term wealth and fulfillment.

Overall, this episode blends real estate tactics, life philosophy, and inspirational storytelling—offering both practical strategies and mindset shifts for investors at any stage.

When Tony Stern, President of PropertyOnion entered real estate, he found a broken system — messy foreclosure data, hidden opportunities, and barriers for small investors. So he fixed it.

In this episode, Tony explains how PropertyOnion started, the technology behind it, and how it’s changing how people buy foreclosures in the U.S.

🔍 Discover how accurate data and community are reshaping property investing.
#PropertyOnion #ForeclosureInvesting #StartupStory


Connect with Jerron:
Jerron Kelley, Esq.
www.kelleygrantlaw.com

Connect with Larry:
Larry Mastropieri
https://www.discoversouthflorida.com

In this episode, we sit down with David Purisch from Horvath & Wemblay to explore how property management strategies adapt to shifting mortgage rates and market conditions. A skilled property manager must navigate interest rates while maintaining steady passive income streams in today's dynamic housing market. Our discussion emphasizes the importance of financial education for both property owners and managers to make informed decisions in the current environment.

In this episode of "Real Deal Investing", hosts Jerron Kelley, a seasoned real estate attorney, and Larry Mastropieri, a real estate broker and agent, talk with Danny Schwab, the CEO and Owner of KeyRenter South Florida.

The discussions explore various aspects of real estate investment and property management, with a strong focus on building solid relationships, understanding tenants' needs, and creating effective management strategies. Danny, an experienced property manager, emphasizes the importance of patience and empathy when dealing with difficult tenant situations, including evictions and financial hardships. He shares stories where he helped tenants avoid eviction through creative solutions like “cash for keys,” aiming to maintain respectful, professional relationships while ensuring his properties are well-managed.

Danny stresses the value of thorough lease customization, learning from each unique situation to create a “living document” that addresses specific issues and responsibilities clearly. He believes that managing tenants well means educating them and adapting the lease based on real experiences, which ultimately fosters trust and mutual respect. When acquiring new properties, he sees proper screening and understanding of tenants’ backgrounds as essential to avoid future conflicts.

Looking to the future, Danny plans to expand his property management business in Florida, aiming to bridge operations between Jacksonville and South Florida through strategic acquisitions. His long-term goals include more real estate development, particularly transforming neglected properties into valuable assets, which he finds fulfilling.

Throughout, Danny highlights the importance of a strong support network, including reliable attorneys, real estate brokers, and a well-trained team. He attributes much of his success to these partnerships, along with a personal commitment to honest communication and consistent client referrals. In addition, Danny’s involvement in networks like BNI has helped him build connections and expand his business. Ultimately, his approach combines practical strategies with a people-centered perspective, allowing him to create positive outcomes for tenants and investors alike.

In this episode of "Real Deal Investing", hosts Jerron Kelley, a seasoned real estate attorney, talk with Phil Kessler of the Property Onion Academy. Phil introduces tax lien and tax deed investing, focusing on Florida's tax-defaulted properties.

Kessler explains the basics: tax liens are essentially loans to property owners who haven't paid their taxes, allowing investors to earn interest over a set period. For instance, if a homeowner in Florida fails to pay property taxes, investors can buy a lien, earning up to 18% interest. If unpaid after two years, investors can initiate a foreclosure through a tax deed sale, where the property may be auctioned to recoup the lien and interest.

Tax deeds, on the other hand, grant direct ownership of a property through foreclosure after unpaid taxes. During auctions, existing mortgages and certain liens are wiped clean, except government liens. Kessler emphasizes that tax liens offer a lower-risk entry into real estate investing because they generally represent a small percentage of the property’s value. This relatively safer, high-yield investment option, traditionally dominated by hedge funds, is now more accessible to individual investors.

Overall, Kessler stresses the importance of thorough research and strategic bidding. He stresses that tax lien and tax deed investments can offer potentially profitable returns but require careful management to mitigate risks.

In this episode of "Real Deal Investing", hosts Jerron Kelley, a seasoned real estate attorney, and Larry Mastropieri, a real estate broker and agent, talk with Quentin Wendt from PadSplit.

The discussion revolves around the innovative PadSplit business model centered around co-living arrangements aimed at providing affordable housing. Quentin begins by outlining how PadSplit operates, allowing investors to optimize revenue by converting single-family homes into multi-room rentals, where each bedroom is rented individually. This approach transforms underutilized spaces—like dining rooms and dens—into additional bedrooms, maximizing income for property owners.

PadSplit primarily serves individuals earning $80,000 or less, providing a digital platform akin to Airbnb but with a focus on longer-term rentals. Unlike short-term vacation rentals, PadSplit boasts an average stay of around nine months, which ensures greater stability and consistent demand for affordable housing. Quentin elaborates on the operational side, noting that successful investors must excel in both property acquisition and management.

The discussion further explores how PadSplit has been beneficial for both multifamily and single-family properties. For struggling multifamily units, converting them into co-living spaces can stabilize revenues by increasing occupancy rates. For example, a two-bedroom apartment traditionally renting for $1,800 can generate up to $3,000 by renting each bedroom separately. However, the model proves especially lucrative for single-family homes, where owners can add extra bedrooms, thus creating a diversified income stream that can prevent zero-revenue months, even with vacant rooms.

Quentin emphasizes PadSplit’s streamlined management system, which handles essential aspects like member bookings, rent collection, and communication, making it less labor-intensive than traditional short-term rental models. This approach is particularly appealing in light of shifting legislation affecting short-term rentals, offering property owners a viable alternative.

The discussion also addresses common challenges in the rental market, particularly regarding tenant expectations and community rules in co-living environments. The importance of thorough background checks and clear communication was stressed to maintain harmony among tenants. Additionally, Quentin discusses exit strategies for investors, including selling properties within the PadSplit marketplace and how transparency in occupancy and revenue data can aid informed investment decisions.

In this episode of "Real Deal Investing", host Jerron Kelley, a seasoned real estate attorney talk with Kim Lochridge, an expert in cost segregation and tax strategies for real estate investors.

Kim is from Engineered Tax Services and she shares invaluable insights on tax savings strategies specifically designed for sophisticated real estate investors. Kim, an experienced investor herself, highlights the importance of cost segregation, a method of accelerated depreciation that allows property owners to categorize and depreciate assets within a property more rapidly than traditional methods. Unlike standard straight-line depreciation, which spans 39 years for commercial properties and 27.5 years for residential ones, cost segregation enables investors to write off components like carpets and HVAC systems over shorter periods—sometimes as little as five years.

The discussion clarifies common misconceptions about cost segregation, emphasizing that it applies exclusively to income-generating properties, not primary residences. Kim underscores the importance of engaging engineers to conduct cost segregation studies, as they are essential for accurately assessing the value of various components within a property. Additionally, she explains the IRS’s preferred methods and guidelines for cost segregation, reinforcing the method’s legitimacy and potential tax benefits.

Furthermore, Kim discusses eligibility for cost segregation studies, which can apply to new constructions, renovations over $50,000, and even improvements in leased spaces. She reassures attendees that even if they missed the opportunity to apply cost segregation at the time of purchase, they can still benefit from it retroactively.

Kim's presentation serves as a comprehensive guide for real estate investors looking to maximize their tax savings through effective strategies like cost segregation and bonus depreciation.

In this episode of "Real Deal Investing", hosts Jerron Kelley, a seasoned real estate attorney, and Larry Mastropieri, a real estate broker and agent, talk with Bryan Cogliano.

Bryan focuses on investment strategies involving Delaware Statutory Trusts (DSTs) and 1031 exchanges, emphasizing the importance of tax deferral and informed decision-making for real estate investors.

Bryan begins by addressing common dilemmas faced by investors, particularly those who feel stuck between selling their properties or continuing to manage them. With limited supply, many investors are finding premium prices for their properties, leading them to sell while preserving tax advantages and maintaining flexibility for future investments.

A key point is the varying hold times for DSTs, with one sponsor targeting a three-year hold, although the standard industry practice tends to be five to six years. Market conditions can influence these hold times significantly. For instance, a Florida multifamily development achieved a favorable offer after just three years, allowing investors to earn over a 20% internal rate of return (IRR). Conversely, in a different scenario, investors may find themselves waiting longer if market conditions are not conducive to selling.

Bryan also delves into the fees associated with 1031 exchanges, noting that intermediary services typically cost between $750 and a few thousand dollars. Importantly, investors often don’t incur out-of-pocket expenses for advisory services, as compensation usually comes from the sponsor companies. Professionals in the field emphasize their role in adding value through referrals and expertise, helping clients navigate complex transactions and avoid substantial tax liabilities.

Finally, the conversation underscores the necessity of understanding tax-saving opportunities and the complexities of real estate investments. It highlights the importance of building strong client relationships based on value, knowledge, and effective communication, ensuring that investors are well-equipped to make informed decisions regarding their financial futures.