Real Estate Investing with RealDealCrew

By RealDealCrew / Jack HossBusiness Entrepreneurship Investing

Real Estate Investing with RealDealCrew episodes

June 11Your CPA Is Costing You Money (Here's Proof) w/ Peter Holtz
Peter Holtz reveals why most CPAs are compliance fillers, not tax planners — and how real estate investors can cut their tax bill by 40% or more.
In this episode of RealDealChat, Jack Hoss sits down with Peter Holtz, certified tax planner and CPA, to break down the massive gap between tax compliance and real estate tax planning strategy.
Peter covers:
Why only 1,100 out of 1.2 million licensed tax preparers are certified tax planners
How cost segregation works and why virtually no one uses it
The 1031 exchange and reverse 1031 you should know before every sale
How a retired real estate investor legally captured $250,000 in tax-free gains every two years
The airline pilot case study: how Peter fought the IRS and won, getting his client years of zero tax liability
Why your CPA saying "no, you can't" is a red flag
How to use real estate depreciation to shelter business income
The McDonald's model and why every successful business is really a real estate business
How Peter's team uses AI and cloud accounting to deliver faster results
Questions you should ask your CPA before you file another return

If you own real estate, run a business, or are paying more taxes than you think you should, this episode is required listening.
🔗 Learn more at: https://go.peterholtzcpa.com/realdealchat
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #TaxPlanning #CostSegregation #1031Exchange #RealDealChat #SmallBusinessTax #TaxStrategy #CPA #RealEstateTax #PassiveIncome #WealthBuilding #TaxFreeIncome
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
32 min
June 09Stop Using AI Like Google (Do This Instead) w/ Michelle Hamilton
Michelle Hamilton reveals how real estate investors are underusing AI and the exact strategies to automate intelligence, decisions, and deal flow.
In this episode of RealDealChat, Jack Hoss sits down with Michelle Hamilton, global AI adoption leader at Answer Rocket, to break down what separates investors who are actually winning with AI from those just typing questions into a chat window.
Michelle brings 30 years of commercial real estate experience to her current role leading enterprise AI adoption and change management. She makes the case that AI underperformance is a people problem, not a technology problem.
What we cover:
Why most investors use AI like a "hyper-Google" and how to stop
Human-first AI adoption and what bottom-up strategy actually means
How large property management firms are onboarding resistant employees
Agentic AI that logs in as you and pulls competitive deal intelligence overnight
Using AI to build predictive dashboards from your existing data
The "smart intern" framework for prompting AI to analyze investment documents
How to use multiple AI models to fact-check each other
Building a synthetic board of directors using voice mode
ChatGPT vs. Gemini vs. Claude: what each model is actually best at
Meta-prompting: asking the model to teach you how to use it
Why the $20/month paid upgrade is worth it and which model to start with
How Michelle's AI chief of staff (George) runs her entire morning

This episode is for:
Real estate investors and syndicators who know they should be using AI but don't know where to start
Operators and business owners sitting on untapped data
Anyone who has tried AI tools and walked away frustrated

If you're ready to go from basic chatbot use to building actual systems around AI, this is the episode.
🔗 Connect with Michelle on LinkedIn: Michelle-Hamilton-AI
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #AIForBusiness #RealDealChat #MultifamilyInvesting #AIAdoption #RealEstateInvestor #ChatGPT #InvestorMindset #BusinessAutomation #PropTech #AIStrategy #Shorts
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
36 min
June 07Why High Earners Still Live Paycheck to Paycheck w/ Andrew Giancola
Andrew Giancola explains why high earners still live paycheck to paycheck and the exact steps to build wealth the right way as a real estate investor.
In this episode of RealDealChat, Jack Hoss sits down with Andrew Giancola of Master Money to break down the financial mistakes even successful investors make and how to fix them before they cost you years of progress.
Andrew covers:
Why lifestyle inflation is the #1 wealth killer for real estate investors
The "Big Three" spending categories that destroy financial progress (housing, transportation, food)
How to find a real tax strategist (not just someone filling in boxes)
The Augusta Rule, cost segregation, and other tax strategies investors overlook
The One-Three-Six emergency fund method and why you need it before you scale
How to calculate your financial freedom number and reverse engineer your portfolio
Avalanche vs snowball method for eliminating consumer debt
Why diversification beyond real estate matters for long-term wealth
How Andrew used AI (including Claude) to build custom software tools in 90 minutes that would have cost $5,000-$10,000
AI use cases for real estate investors: property evaluation, tenant management, and deal analysis

This conversation is essential for:
Real estate investors who feel busy but not financially free
Entrepreneurs scaling income but not building wealth
Investors who want to clean up their financial foundation before they grow

If you've ever made more money and somehow ended up with less, this episode will show you exactly where it's going and how to stop it.
🔗 Learn more about Andrew: https://mastermoney.co
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #WealthBuilding #PersonalFinance #LifestyleInflation #TaxStrategy #FinancialFreedom #RealDealChat #InvestorMindset #PassiveIncome #AIForBusiness
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
36 min
June 05Why 90% of ISA Hires Fail Before They Start w/ Gustavo Munoz Castro
Gus Munoz-Castro reveals why 90% of ISA hires fail — and how real estate investors can use AI to train callers, scale lead gen, and close more deals.
Full Description
In this episode of RealDealChat, Jack Hoss sits down with Gustavo Munoz-Castro of Power ISA to break down how real estate investors can build high-performing calling teams, use AI the right way, and stop wasting money on lead gen strategies that don't convert.
Gus has been in the ISA and virtual assistant space for over five years and shares what's actually working right now in today's market.
Topics covered:
Why 90% of ISA success or failure is determined before you ever hire someone
How AI voice agents are being used to train callers instead of replace them
The 10X coaching efficiency unlock: feedback sessions with 5-10 people in the time it used to take for one
Why cold calling, mailers, and driving for dollars still work better than ever
The real problem with Google Pay Per Click for real estate investors
How to build a lead gen system before you add any leverage
What the 45X ROI calling case study looked like in practice
The "3 motivated sellers a day" rule and why it compounds
How to script calls: intro and close from memory, bullet points for everything else
Why genuine curiosity and rapport are the two things you can't train around

If you are trying to scale your acquisitions, this episode cuts through the AI hype and gives you a clear framework for building the systems and the team to back it up.
🌐 Learn how Power ISA can help your team: https://powerisa.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #ISA #VirtualAssistants #LeadGeneration #ColdCalling #RealDealChat #AIForBusiness #WholesaleRealEstate #MotivatedSellers #RealEstateInvestor
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
37 min
June 03Why Your CPA Is Costing You Money (And Doesn't Know It) w/ Kevin Brunner
Kevin Brunner explains why your CPA may be costing you money, how to cut your effective tax rate, and what most real estate investors get wrong about wealth preservation.
In this episode of RealDealChat, Jack Hoss sits down with Kevin Brunner of The Q Companies to talk about what happens to a real estate portfolio when the wrong advisors are in place, and what it looks like to actually protect the wealth you've built.
Kevin breaks down:
Why CPAs advise investors to "just pay the tax" and how that costs you money every year
How high-earning investors can stay at a 10% effective federal tax rate
The installment sale trust strategy and how it avoids capital gains on a sale
Why a 1031 exchange alone is not a complete exit strategy
How to reset depreciation through a trust structure
What "hold till you die, swap till you drop" really means for your portfolio
Why the financial services industry is set up against the investor
How to prepare your heirs to actually manage what you leave them
Why wealth transferred without preparation destroys families
The "quadrant" framework for thinking about all your assets, not just financial ones

This episode is for:
Real estate investors with significant equity who haven't updated their estate plan
Investors approaching a sale or 1031 exchange
Anyone who suspects their advisor isn't giving them the full picture
Portfolio holders who haven't thought about succession and heir preparation

🔗 Learn more about Kevin and The Q Companies: https://theqcompanies.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #TaxStrategy #WealthPreservation #EstatePlanning #1031Exchange #PassiveIncome #RealDealChat #InvestorMindset #FinancialAdvisor #TaxEfficiency
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
44 min
June 01Stop Chasing Clients: Build a Brand That Attracts Them w/ Tara Polley
Tara Polley explains how building a personal brand through media stopped the grind and started attracting clients who already trust her.
In this episode of RealDealChat, Jack Hoss sits down with Tara Polley of welcomehomesonoma.com, a 25-year real estate veteran turned television host, to break down how media, storytelling, and personal brand building change the game for realtors and investors alike.
Tara shares her full framework including:
Why getting on camera shortens the sales cycle by building trust before the first conversation
How storytelling and authenticity outperform polished, perfect content every time
The role AI tools like Claude and ChatGPT play in scripting listings and TV segments
How she uses CapCut and TikTok to create social content fast without a big production team
Why lifestyle marketing sells properties faster than leading with features and square footage
The delegation framework she uses to decide what to keep vs. automate vs. hand off
What top performers in real estate actually have in common (and it's not talent)
Why realtors who stay stuck in 2021 pricing mindsets are losing deals right now

This episode is for:
Realtors ready to stop cold prospecting and start attracting aligned clients
Investors who want to understand how personal brand impacts deal flow
Anyone in real estate who knows they should be creating content but keeps putting it off

If you've ever felt like you were grinding harder than your results showed, this episode is the reset you need.
🔗 Check out Tara: https://welcomehomesonoma.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateMarketing #PersonalBrand #RealtorLife #RealEstateInvesting #ContentMarketing #RealDealChat #AIForRealEstate #SocialMediaForRealtors #RealEstateBusiness #ClientAttraction
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
29 min
May 30This $50 Billion Plan Could Rebuild Detroit w/ Rod Lockwood
Rod Lockwood reveals his $50 billion plan to transform Belle Isle into a tax-free, self-governing city — and what it means for Detroit real estate investors.
In this episode of RealDealChat, Jack Hoss sits down with Rod Lockwood, a second-generation Detroit real estate developer and founder of the Belle Isle Freedom City project — a bold proposal to turn a 1,000-acre island in the Detroit River into a privately funded, tax-free, self-governing city of 50,000 people.
Rod breaks down:
Why Detroit went from the richest city in the world in 1950 to the poorest major city today
The 99-year lease structure modeled after Hong Kong's revival
How Belle Isle would operate with no income tax and a land value tax system
Why 46,000 Detroiters would commute to the island daily, paying full state and federal taxes
The estimated $5 to $6 billion infrastructure investment and $50 billion total build-out
How Detroit land at $7 to $10 per square foot becomes attractive to international entrepreneurs
The Formula One racetrack concept and car-free design
Why a commissioned poll showed Detroit residents support the project by a plus 41% margin
How Rod is using AI for cost modeling and document prep across the project

This episode is for investors watching the Detroit market, anyone interested in special economic zones, and real estate developers thinking about large-scale opportunity and urban policy.
🔗 Learn more about the project: https://bellisle-freedomcity.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #Detroit #SpecialEconomicZone #LandValueTax #FreedCity #UrbanDevelopment #RealDealChat #InvestorMindset #AffordableHousing #RealEstateDevelopment
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
33 min
May 28Why Paying Off Your Mortgage Is Killing Your Wealth w/ Al Zdenek
Al Zdenek explains why paying off your mortgage early could be destroying your long-term wealth and how to reach financial freedom faster by thinking differently.
In this episode of RealDealChat, Jack Hoss sits down with Al Zdenek, CPA, wealth advisor, and author of Master Your Cash Flow, to break down the financial decisions most investors and business owners are getting completely wrong.
Al went from near-bankruptcy in his 30s with tens of millions in troubled projects, to reaching financial independence at 48. Now he shares the exact framework he used with hundreds of clients to accelerate their path to financial freedom.
What you'll learn in this episode:
Why paying off your mortgage early can actually leave you broke in retirement
The difference between good debt and bad debt (and why most gurus blur the line)
How small financial decisions today compound into massive outcomes over decades
The right way to negotiate $100K in credit card debt down to near zero interest
Why going into retirement with a paid-off house can be a financial trap
How Al helped a former Fortune 500 president restart his retirement cash flow overnight
What most financial advisors are missing because they only think short-term
Why cash flow-oriented advising beats goals-based advising every time
How to know if you could retire 5 to 10 years earlier than you think

This episode is essential for:
Real estate investors balancing good debt vs. equity
Business owners approaching retirement
Anyone who's been told to pay off debt first and save
Investors who want to use leverage strategically instead of emotionally

If you've ever wondered whether you're actually building wealth or just feeling like it, this episode will change how you think.
🔗 Learn more from Al: https://alzenek.com
🔗 Check out the CakeClub app: https://cakeclubapp.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #FinancialFreedom #WealthBuilding #CashFlow #GoodDebt #RealDealChat #PersonalFinance #RetirementPlanning #InvestorMindset #DebtStrategy #FinancialIndependence #RealEstatePodcast
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
46 min
May 26Why Out-of-State Investors Are Quietly Building Wealth in Detroit w/ Voytek Mardula & James Lloyd
Voytek Mardula and James Lloyd explain how out-of-state investors are building cash-flowing rental portfolios in Detroit with full turnkey support.
In this episode of RealDealChat, Jack Hoss sits down with Voytek Mardula and James Lloyd of usproperties.ca, a fully turnkey real estate operation that has bought, renovated, and sold over 600 homes in the Detroit market over nine years.
What started as their own search for cash flow in an expensive Canadian market turned into one of the most comprehensive turnkey operations serving out-of-state and international investors. They break down exactly how they source, renovate, manage, and scale properties for their clients, including a growing short-term rental division that is outperforming expectations with AI-powered pricing.
Key topics covered:
Why Detroit is still one of the most undervalued real estate markets in the country
How Voytek and James identify B and B-plus neighborhoods with double-digit appreciation potential
Why they focus exclusively on single-family homes over multifamily and what they learned the hard way
The Section 8 strategy that held strong through COVID and recessionary periods
How their short-term rental division works, including fully furnished turnkey packages at 15% management
The AI pricing software that increased bookings immediately after launch and why it removes the emotional "race to the bottom" in STR pricing
BRRRR and DSCR lending strategies to recycle equity into more doors within 18 to 24 months
Real investor stories: clients who reached 12 to 13 properties and got all their initial capital back through refinances
How AI voice agents are changing their investor intake and customer service operations

If you are sitting on capital and looking for an affordable market with real cash flow, genuine appreciation, and a team that handles everything, this episode is the blueprint.
🔗 Learn more about Voytek and James: https://usproperties.ca
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #DetroitRealEstate #TurnkeyInvesting #CashFlowInvesting #OutOfStateInvesting #ShortTermRentals #BRRRRStrategy #Section8Investing #PassiveIncome #RealDealChat #RentalPortfolio #AIForBusiness
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
41 min
May 24Buy Vacant Land and Flip Brand New Mobile Homes for $40K Profit w/ Chris Gavre
Chris Gavre breaks down how to buy vacant land and flip brand new mobile homes for $40K per deal using FHA financing and a repeatable 4-month system.
In this episode of RealDealChat, Jack Hoss sits down with Chris Gavre of The Land Sharks to unpack one of the most underrated strategies in real estate investing right now: buying raw vacant land, placing a brand new manufactured home on it, making it FHA compliant, and selling it for $40,000+ in net profit per deal.
Chris and his partner Robert have done 50-60 of these in a single year with a lean two-person operation.
Topics covered in this episode:
Why this strategy out-performs traditional house flipping on predictability and margins
How to source vacant land using zoned and filtered county data
The FHA compliance process: detitling, brick skirting, and the engineer certification
What a double wide costs wholesale from manufacturers like Clayton and Champion ($62-72K)
How to net $40-45K per deal with total development costs around $40-50K
The 4-month timeline from land purchase to closed sale
Why 95% of buyers use FHA financing and what that means for your exit
How to fund these deals when hard money lenders have never heard of the strategy
Running 18-19 simultaneous projects with just two people
The zoning, septic, and permitting process broken down step by step
Why direct mail pulls better leads than cold calling for this buy box

If you're a real estate investor looking for a predictable, scalable alternative to house flipping or new construction, this episode is worth a listen.
🔗 Learn more: https://thelandsharks.com
🔗 Build systems for your investing business: https://realdealcrew.com
#RealEstateInvesting #MobileHomeInvesting #ManufacturedHousing #AffordableHousing #LandInvesting #HouseFlipping #RealDealChat #Shorts #PassiveIncome #FHALoans #RealEstateStrategy #LandDevelopment
Work With RealDealCrew
If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:
Take the Deal Intake Assessment
See how resilient your current operation actually is.
→ https://assessment.realdealcrew.com
Book a Fit Call
If you want to explore what a fully system-driven deal flow looks like, let’s talk.
→ https://realdealcrew.com/book
LIKE • SHARE • JOIN • REVIEW
Website
Apple Podcasts
YouTube
YouTube Music
Spotify
Amazon Music
Facebook
Twitter
Instagram
32 min

About Real Estate Investing with RealDealCrew

From the publisher's feed

Real Estate Investing with RealDealCrew is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals.