Real Estate Investing with RealDealChat

Jack Hoss reveals his new plan to rebuild his real estate websites using funnels, automation, and smarter SEO to save time and close more deals. YouTube Video at: https://youtu.be/Hco058Q4GY4 In this episode of RealDealCast , Jack Hoss breaks down his complete plan to rebuild and streamline his real estate web presence for better lead generation and automation. After seeing a drop in search rankin...

Robin Kencel shares powerful negotiation strategies from her luxury real estate career, teaching how mindset, rhythm, and empathy drive better deals. In this episode of RealDealChat , Jack Hoss sits down with Robin Kencel , top Greenwich, CT real estate agent, ballroom dancer, and negotiation coach, to explore what it takes to master negotiation — in business, relationships, and life. Robin shares...

Alec McElhhiny shares how he scaled from house hacking a duplex to developing high-profit flex spaces through LandPlay.com and creative land deals. In this episode of RealDealChat , Jack Hoss sits down with Alec McElhhiny , founder of LandPlay.com , to discuss how he went from an actuary crunching numbers to a real estate developer building niche flex space projects across Texas. Alec breaks down...

Debbi DiMaggio shares her 35-year real-estate journey, mindset strategies, and how AI & authenticity help agents and investors thrive in any market. In this episode of RealDealChat , Jack Hoss sits down with Debbi DiMaggio — luxury real-estate icon, author, speaker, and coach at CoachWithDebbi.com — to unpack the habits, mindset, and authenticity that built her 35-year career. Debbi reveals ho...

Jack Hoss compares the top AI vibe coding tools—V0, Bolt, Replit, and Lovable—to find the fastest, easiest way to build real estate funnels. In this RealDealCast episode, Jack Hoss tests four of the most talked-about AI website-building platforms — V0, Bolt, Replit, and Lovable — to see which one actually delivers the best results. He gives each platform the same prompt and compares the output, la...

Attorney Luke Carlson explains how homeowners and investors can protect themselves from bad HOAs, understand their rights, and turn risk into opportunity. In this episode of RealDealChat , Jack Hoss sits down with Luke Carlson , founding attorney of LS Carlson Law and author of The Homeowner’s Guide to Defending Against Bad HOAs , to uncover what every real estate investor and homeowner needs to k...

Cody Hofhine shares how to build a 7-figure wholesaling business, lead better teams, and buy back your time through delegation, systems, and mindset. In this episode of RealDealChat , Jack sits down with Cody Hofhine , co-founder of Joe Homebuyer and former leader of Wholesaling Inc. , to talk about how to grow a real estate business that gives you time freedom — not just financial success. Cody b...

Max Emory shares how real estate investors can simplify bookkeeping, avoid IRS headaches, and create “decision-ready” financials to grow their profits. In this episode of RealDealChat , Jack Hoss sits down with Max Emory , founder of Time Capital Bookkeeping , to discuss how real estate investors can master their numbers, avoid tax-time chaos, and make smarter decisions using clean, actionable fin...

Ladislas Maurice, “The Wandering Investor,” shares how to build global freedom through international real estate, second passports, and frontier markets. In this episode of RealDealChat , Jack sits down with Ladislas Maurice , founder of The Wandering Investor , to discuss the power of international investing and how real estate can become your ticket to global diversification, second citizenship,...

Franchise expert Kim Daly explains how real estate investors can build scalable, semi-active businesses that create wealth, freedom, and long-term cash flow. In this episode of RealDealChat , Jack sits down with Kim Daly , founder of The Daly Coach and one of the top franchise consultants in the U.S., to talk about how real estate investors can use franchising to diversify their portfolios and cre...

Learn how cost segregation helps real estate investors save thousands in taxes. In this video, Gian Pazzia of KBKG breaks down how bonus depreciation , 1031 exchanges , and other real estate tax strategies can accelerate your wealth-building plan. In this episode of RealDealChat , Jack Hoss interviews Gian Pazzia , CCSP and President of KBKG — creators of CostSegregation.com — to uncover how inves...

George Dimov, CPA, shares the biggest tax mistakes real estate investors make, why proactive planning matters, and how to build smarter portfolios. In this episode of RealDealChat , Jack sits down with George Dimov , CPA and founder of DimovTax.com, to discuss proactive tax planning, common mistakes investors make, and why accounting + real estate go hand in hand. George shares his journey from im...

Katie Kim shares how she turned a $50K bakery investment into a $5.5M project, scaled her family business, and now teaches others to develop smarter. In this episode of RealDealChat , Jack sits down with Katie Kim , real estate developer, CCIM, and founder of The Kim Group , to talk about her journey from growing up in a construction family to leading multimillion-dollar development projects. Kati...

David Christensen shares how storytelling, mindset, and authenticity helped him sell 400+ homes, including the Breaking Bad house, and rebuild his life. In this episode of RealDealChat , Jack sits down with David Christensen ( DavidChristensen.com ) to discuss his extraordinary journey—from managing platinum-selling musicians and even working on Titanic research dives, to becoming a nationally rec...

Gideon Spencer shares how he scaled from a cash-flowing fourplex to $6M in boutique hotels using automation, creative financing, and the mentor flywheel. In this episode of RealDealChat , Jack sits down with Gideon Spencer , real estate investor and founder of a new boutique hotel community, to discuss how he scaled from a fourplex short-term rental to multi-million-dollar boutique hotels in just...

Claude Sonnet 4.5 brings powerful AI agents, coding tools, and automation upgrades—here’s how real estate investors can use them to save time. In this episode of RealDealCast , Jack Hoss breaks down Anthropic’s release of Claude Sonnet 4.5 and what it means for real estate professionals. From AI agents that can run tasks for 30+ hours straight to improved coding, automation, and Chrome extensions,...

Mark Ainley shares his journey from BRRRRs to running GC Realty, scaling property management in Chicago, and lessons from 20+ years in real estate. In this episode of RealDealChat , Jack sits down with Mark Ainley , co-founder of GC Realty & Development , co-host of Straight Up Chicago Investor Podcast , and long-time property manager and investor. Mark shares how he transitioned from house ha...

Shawn Griffith of Kraft Capital explains why no investor should ever be passive, how to underwrite risk, and why multifamily is a long-term wealth game. In this episode of RealDealChat , Jack sits down with Shawn Griffith , managing partner at Kraft Capital Investments , to discuss the reality of multifamily investing, the dangers of being a “passive investor,” and why risk management is the corne...

Discover time-saving AI tools and tech tips for real estate investors in this episode of RealDealCast. From enhancing thumbnails to generating professional headshots, Jack Hoss explores Google’s Nano Banana AI and other automation tools that can save investors valuable time. In this solo session, Jack shares real-world use cases—improving podcast thumbnails, designing hero banners, cleaning up hea...

Henry Yoshida of Rocket Dollar explains how to use IRAs for real estate, crypto, and private deals—unlocking $18T in retirement funds for alternatives. In this episode of RealDealChat , Jack sits down with Henry Yoshida , co-founder & CEO of Rocket Dollar (a subsidiary of Retired.com), to explore how investors can unlock the power of retirement accounts for real estate, crypto, and private inv...

Patrick Pychynski reveals how to access $50K–$250K in 0% business credit, avoid high-interest traps, and become bankable for long-term success. In this episode of RealDealChat , Jack sits down with Patrick Pychynski , founder of StackingSuccess.com, to discuss how entrepreneurs and real estate investors can unlock business funding the right way. Patrick shares his journey from the U.S. Marine Corp...

Michael Root shares how he builds value in Chicago multifamily, streamlines property management, and uses in-house contracting to boost efficiency. In this episode of RealDealChat , Jack sits down with Michael Root , co-founder of Root Property Group (RootPG.com) , to discuss property management, multifamily acquisitions, and why Chicago remains both a challenging and rewarding market. Michael sha...

Mikkel Thorup shares how he built an 8-figure global real estate portfolio, lives in 9 countries, and helps investors create offshore wealth strategies. In this episode of RealDealChat, Jack sits down with Mikkel Thorup, host of the Expat Money Show and founder of ExpatMoney.com Mikkel shares his inspiring journey from being labeled with a “learning disability” and dropping out of school at 15, to...

Dedric & Krystal Polite share how they built a real estate empire, landed a Hulu TV show, and created a wealth education platform for new investors. In this episode of RealDealChat , Jack sits down with Dedric & Krystal Polite , stars of Hulu’s 50/50 Flip and founders of Polite Wealth Portal , to discuss their journey from 9–5 jobs to becoming respected real estate investors, educators, an...

Paul Cecil of ReAlpha shares how AI, commission rebates, and acquisitions are disrupting home buying—and what it means for buyers and investors. In this episode of RealDealChat, Jack sits down with Paul Cecil, President of ReAlpha (NASDAQ: AIRE), to discuss how his company is transforming real estate through AI and innovative business models. Paul explains how ReAlpha offers up to 80% of the buy-s...