Real Estate Investing with RealDealChat
Real Estate Investing with RealDealChat is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals. Each episode breaks down: • Real estate investing strategies • Deal sourcing and wholesaling tactics • Fix and flip systems • Rental property scaling • AI and automation tools for investors • Deal operations and lead management Hosted by Jack Hoss, a real estate investor and founder of RealDealCrew, the show focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow...
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Lane Kawaoka
<p>Work With RealDealCrew</p><p>If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:</p><p>Take the Deal Intake Assessment</p><p>See how resilient your current operation actually is.</p><p>→ https://assessment.realdealcrew.com</p><p>Book a Fit Call</p><p>If you want to explore what a fully system-driven deal flow looks like, let’s talk.</p><p>→ https://realdealcrew.com/book</p><p>LIKE • SHARE • JOIN • REVIEW</p>WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram<br/>
Transforming Real Estate Investing into a Business w/ Mark Molin
<p>In this conversation, Mark Mullen discusses the importance of treating real estate investing as a serious business. He emphasizes the role of a CFO in managing finances, the need for detailed financial tracking, and the significance of collaboration and communication in real estate projects. Mark shares insights on profit margins in fix and flipping, the value of performance-based CFO services, and the lessons learned from mistakes in business. He concludes with advice on building strong relationships and strategies for financial safety in real estate investing.</p><p>Takeaways</p>Real estate investing requires a structured financial approach.A CFO...
Mastering Passive Investing: Insights from Patrick Grimes
<p>In this conversation, Patrick Grimes shares his journey from a corporate engineering background to becoming a successful entrepreneur and passive investor. He discusses the importance of time freedom, the transition to passive investing, and the significance of diversification in building a resilient investment portfolio. Patrick also delves into the role of AI in enhancing business processes and the importance of non-correlated investments, particularly in healthcare. The discussion highlights the challenges and lessons learned in scaling a business and the value of partnerships in achieving financial security.</p><p>Takeaways</p>Time freedom and location freedom are essential for a...
From Wall Street to Short-Term Rentals: A Journey w/ Michael Chang
<p>In this conversation, Michael Chang shares his journey from a successful career in investment banking on Wall Street to becoming a thriving entrepreneur in the short-term rental market. He discusses the challenges and lessons learned from his transition, including the importance of flexibility, the impact of technology, and the financial benefits of short-term rentals compared to traditional long-term investments. Michael also delves into the STR tax loophole, market saturation, and the significance of quality in real estate investments. He emphasizes the need for self-belief and the value of surrounding oneself with supportive networks in the entrepreneurial journey.</p><p>...
The Portugal Golden Visa: A Path to Residency w/ Daniel Daly
<p>In this conversation, Daniel Daly shares his journey from the automotive industry to real estate investment, focusing on international opportunities, particularly in Portugal. He discusses the advantages of the Portugal Golden Visa program, the challenges of building a network abroad, and the importance of customer experience in hospitality. Daniel emphasizes the need for effective delegation and the impact of tourism on property values in Europe. He also addresses the evolving regulations in real estate investment and the benefits of having a visa or citizenship in another country, especially for retirement.</p><p>Takeaways</p>Bringing an outside perspective can...
Nearshore vs Offshore Talent: What Actually Works w/ Brian Samson
<p>Brian Sampson breaks down nearshore vs offshore talent, critical thinking vs scripted VAs, and how Latin America teams create true ROI for real estate operators.</p><p>In this episode of RealDealChat, Jack Hoss sits down with Brian Sampson, co-founder of PLUG, to unpack the real differences between offshore, nearshore, and onshore talent — and why it matters more than ever in the age of AI.</p><p>If you’re a real estate investor, realtor, or operator using virtual assistants, this conversation will challenge how you think about cost savings versus business multiplication.</p><p>We cover:</p>Offshore vs n...
Why Most Real Estate Investors Plateau with John Donnelly
<p>John Donnelly shares why most real estate investors plateau — and the mindset, systems, and accountability needed to break through.</p><p>In this episode of RealDealChat, John Donnelly joins Jack to unpack a problem most investors quietly face: growth ceilings.</p><p>We explore why operators often stall after early wins, how identity and self-concept cap performance, and why systems only work when they’re aligned with personal clarity.</p><p>John shares insights on:</p>Breaking through revenue plateausWhy mindset > tactics long termThe danger of chasing strategies without alignmentAccountability and peer environmentsSimplifying instead of stacking complexityWhen to double down...
Why 82% of Homeowners Regret Their Purchase with Kim Costa
<p>Kim Costa explains why 82% of homeowners regret their purchase — and how aligning your home with your identity changes everything.</p><p>In this episode of RealDealChat, Kim Costa — author of Live in Your Wheelhouse and host on The American Dream TV — breaks down the psychology behind real estate decisions.</p><p>Kim introduces her framework built around:</p>The Four M’s (Myself, Mastery, Mission, Mates)The Wheel of Life across 8 key areasWhy most buyers move without clarityThe statistic that 82% of homeowners report regretHow real estate agents can shorten buying cyclesHow AI tools like Claude and ChatGPT help scale contentW...
How to Increase Airbnb Revenue 23% (Without More Units) w/ Dan Rivers
<p>Dan Rivers explains how short-term rental owners can increase Airbnb revenue by 20%+ using listing optimization, pricing strategy, and revenue management.</p><p>In this episode of RealDealChat, Jack Hoss sits down with Dan Rivers, founder of Synergy Stays, to break down what most Airbnb hosts get wrong about revenue management.</p><p>Dan shares how his clients average a 23% revenue lift in year one, and why many operators are unknowingly leaving thousands on the table.</p><p>We cover:</p>The biggest Airbnb listing mistakesWhy professional photography still mattersHow to move from 50th to 75th percentile in your marketLeveraging...
Opportunity Zones Are Permanent: What Investors Need to Know with Ashley Tison
<p>Ashley Tison explains how Opportunity Zones became permanent — and how investors can defer, reduce, and potentially eliminate capital gains taxes.</p><p>In this episode of RealDealChat, Ashley Tison of OZ Pros breaks down Opportunity Zones in plain English — what they are, how they work, and why the recent legislative updates changed the long-term strategy for investors.</p><p>We cover:</p>How Opportunity Zones were created under the Tax Cuts and Jobs ActThe “defer, reduce, eliminate” frameworkWhat the new rolling 10-year election meansHow investors can potentially write down gains before 2026Why long-term holds now outperform IRR-chasing churnReal examples of commu...
