Real Estate Investing with RealDealChat
Real Estate Investing with RealDealChat
RealDealCrew / Jack Hoss

Real Estate Investing with RealDealChat

InvestingBusinessEntrepreneurshipEnglish
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 the show to get weekly insights on real estate investing strategies, deal flow systems, and operational growth.
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The Portugal Golden Visa: A Path to Residency w/ Daniel Daly
09 March 2026

The Portugal Golden Visa: A Path to Residency w/ Daniel Daly

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...
Nearshore vs Offshore Talent: What Actually Works w/ Brian Samson
07 March 2026

Nearshore vs Offshore Talent: What Actually Works w/ Brian Samson

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.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.If you’re a...
Why Most Real Estate Investors Plateau with John Donnelly
05 March 2026

Why Most Real Estate Investors Plateau with John Donnelly

John Donnelly shares why most real estate investors plateau — and the mindset, systems, and accountability needed to break through.In this episode of RealDealChat, John Donnelly joins Jack to unpack a problem most investors quietly face: growth ceilings.We explore why operators often stall after early wins, how identity and self-concept cap performance, and why systems only work when they’re...
Why 82% of Homeowners Regret Their Purchase with Kim Costa
03 March 2026

Why 82% of Homeowners Regret Their Purchase with Kim Costa

Kim Costa explains why 82% of homeowners regret their purchase — and how aligning your home with your identity changes everything.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.Kim introduces her framework built around:The Four M’s (Myself, Mastery, Mission, Mates)The Wheel...
How to Increase Airbnb Revenue 23% (Without More Units) w/ Dan Rivers
01 March 2026

How to Increase Airbnb Revenue 23% (Without More Units) w/ Dan Rivers

Dan Rivers explains how short-term rental owners can increase Airbnb revenue by 20%+ using listing optimization, pricing strategy, and revenue management.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.Dan shares how his clients average a 23% revenue lift in year one, and why...
Opportunity Zones Are Permanent: What Investors Need to Know with Ashley Tison
27 February 2026

Opportunity Zones Are Permanent: What Investors Need to Know with Ashley Tison

Ashley Tison explains how Opportunity Zones became permanent — and how investors can defer, reduce, and potentially eliminate capital gains taxes.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.We cover:How Opportunity Zones...
Why 100% Loan-to-Cost Lending Is Working in the Midwest with Matthew Medrano
25 February 2026

Why 100% Loan-to-Cost Lending Is Working in the Midwest with Matthew Medrano

Matthew Medrano shares how Dynamo Capital scaled from a $5M goal to a $100M+ private credit fund by focusing on speed, alignment, and Midwest lending.In this episode of RealDealChat, Matthew Medrano of Dynamo Capital breaks down how a frustrated mortgage broker built a direct lending fund focused on fast funding, flexible terms, and aligned incentives.We cover:Why Dynamo offers 100% loan-to-cost...
From Wall Street to 500M+ in Apartments: Lessons in Discipline w/ Michael Pouliot
23 February 2026

From Wall Street to 500M+ in Apartments: Lessons in Discipline w/ Michael Pouliot

Michael Pouliot shares why vertical integration, disciplined buy boxes, and patience are key as multifamily heads into a major refinance cycle.In this episode of RealDealChat, Michael Pouliot—fourth-generation real estate entrepreneur and founder of Carbon—breaks down what’s really happening in multifamily as the 2025–2027 maturity wall approaches.We discuss raising capital ahead of distress, why...
Subject-To Real Estate Done Right with Caleb Christopher
21 February 2026

Subject-To Real Estate Done Right with Caleb Christopher

Caleb Christopher breaks down subject-to real estate, wraparound mortgages, and why creative finance without proper structure can destroy deals.In this episode of RealDealChat, Caleb Christopher — self-described “systems nerd” and real estate deal architect — explains how creative finance deals actually work in the real world.We go deep into subject-to transactions, wraparound mortgages,...
How Self Storage Can Offset 50–90% of Your Tax Bill with Fernando Angelucci
19 February 2026

How Self Storage Can Offset 50–90% of Your Tax Bill with Fernando Angelucci

Fernando Angelucci explains how tax-advantaged self storage, solar infrastructure, and AI-driven pricing are reshaping modern real estate returns.Full description:In this episode of RealDealChat, Fernando Angelucci, founder of Self Storage Syndicated Equities, breaks down why self storage continues to outperform—and how investors can use it to reduce taxes while building long-term wealth.Fernando...