Real Estate Investing with RealDealCrew

Brad Baldridge breaks down how real estate investors and business owners can legally reduce college costs — using income control, asset positioning, and tax strategy.

In this episode of RealDealChat, Jack Hoss sits down with Brad Baldridge, financial advisor and college planning specialist at Taming the High Cost of College, to unpack one of the most overlooked financial planning opportunities for real estate investors — using their assets and income control to dramatically reduce what they pay for their kids' college education.

Brad covers:

• Why families come too late — and the ideal planning runway (sophomore year of high school)
• The difference between need-based aid and merit aid — and why elite private schools can actually be cheaper than you think
• Why real estate investors and business owners have levers W-2 employees simply don't have
• How to use income control, bonus timing, and salary adjustments to improve your FAFSA position
• Why investment real estate must be reported as an asset (at net value, not gross) — and what that actually means for your aid calculation
• How to shift income and assets to your student to unlock tax credits that phase out at higher income levels
• Real case study: a teacher's family inherited $500K and still qualified for a full ride by repositioning assets correctly
• Real case study: an engineering manager calculated that paying full price for NYU cost him 3 extra years of work — and decided that was fine
• Why applying to five schools of the same type is one of the most common and costly mistakes families make
• How to vet a college financial advisor — and why most people don't know to ask about the CSS profile vs. FAFSA
• Brad's take on AI: useful for research, not yet replacing expertise — and why the "AI will take all the jobs" panic is overblown
• Niching down: how becoming the college planning specialist transformed Brad's financial advisory practice

This episode is for:

• Real estate investors who have kids approaching college age
• Business owners who want to understand how income control affects financial aid
• Any parent who wants to stop leaving money on the table when paying for college

🔗 Learn more: https://taminghighcostofcollege.com

#CollegePlanning #CollegeCosts #RealEstateInvesting #FinancialPlanning #FAFSAStrategies #RealDealChat #CollegeFinancialAid #BusinessOwner #MeritAid #CollegeSavings

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John Bernard of Southview Timber breaks down timberland investing — how it generates multiple income streams, why the Southeast is the top market, and how to get in.

In this episode of RealDealChat, Jack Hoss sits down with John Bernard, co-founder of Southview Timber and manager of the Southview Timberland Fund, to break down one of the most overlooked asset classes in real estate investing.

John covers:

• Why his family bought timberland in 2008 — and how 15 years at JP Morgan and Wells Fargo led him to democratize the asset class
• Why the Southeast US (Georgia, North Florida, South Carolina, Alabama) is now the #1 timber region in North America
• The three ways a single property can generate returns: timber harvest, real estate appreciation, and development or recreational sale
• How Southview sources deals entirely through personal relationships — and why outsiders simply can't access the same pipeline
• The sweet spot: 200–2,000-acre mid-size properties that fall below institutional radar and above most individual investor budgets
• Underwriting criteria: proximity to mills (within 50 miles), soil productivity, access roads, and multiple buyer options
• Why timberland investors can wait for the best timber prices — unlike farmland, there's no forced harvest
• How demographic migration from the Northeast and West Coast is driving rural land values up in the Southeast
• The 500-acre deal they bought for $1M and exited in 60 days — selling parcels to a business and an adjacent landowner
• Why John is cautious about AI-labeled startup investments — and why he prefers assets you can put boots on the ground to verify
• Current bottleneck: capital. They have deal flow. The fund is nearly deployed and raising toward $50M.

This episode is for:

• Accredited investors looking for non-correlated, tangible alternatives to stocks and crypto
• Real estate investors who want to understand a high-margin niche with multiple exit options
• Family offices and RIAs seeking a conservative real assets strategy

🔗 Learn more: https://southviewtimber.com 🔗 Find John on LinkedIn: John Bernard

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Trevor Mauch of Carrot.com breaks down why more leads isn't the answer, why sellers ghost you, and how AI search is already changing deal flow.

In this episode of RealDealChat, Jack Hoss sits down with Trevor Mauch, founder and CEO of Carrot.com, to zoom out from marketing tactics and talk about where real estate investing, AI, and online trust are actually heading.

Trevor covers:

• The #1 assumption quietly killing investor deal flow — and why optimizing leads beats generating more
• Why "if you're not growing you're dying" is a lie — and the three real reasons business exists
• The difference between a logo and an actual brand — and why 8 out of 10 investors don't have one
• Why sellers ghost you (spoiler: it's almost never about price)
• The "evergreen marketing" principle: how to build lead flow that doesn't require constant feeding
• What a real USP looks like in 2026 — and why "cash offer, close in 7 days" stopped being one years ago
• The AI continuum: from untrained ChatGPT threads to well-trained coaches to autonomous agents
• How Carrot ingests seller call conversations and auto-recommends website updates to close objection gaps
• How Google's AI overviews nearly doubled daily searches — and what that means for your SEO
• Why a guy in Ohio got his first ChatGPT-sourced seller lead within 3 weeks of simple brand updates
• The human-AI balance: using technology to scale humanity, not replace it
• Why efficiency gains from AI tend to create more work, not more freedom — and what to do instead

This episode is for:

• Wholesalers, flippers, and agents who keep spending on leads and not seeing results
• Investors who want to understand how AI search is already changing inbound deal flow
• Anyone building or refining their online presence and brand for 2026

🔗 Learn more at: https://carrot.com 🔗 Trevor's AI Search Challenge: carrot.com

#RealEstateInvesting #LeadGeneration #RealEstateBrand #WholesaleRealEstate #AISearch #RealDealChat #CarrotCom #InvestorMarketing #SellerLeads #RealEstateTips

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

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Charles Gaudet took a business from $950K to $66M in 7 years — and says hard work was the problem, not the solution. Here's the system he built.

In this episode of RealDealChat, Jack Hoss sits down with Charles Gaudet, founder of Predictable Profits and coach to over 2,000 businesses, to break down why most entrepreneurs hit a wall at $1–3M — and the three-system framework that breaks through it.

Charles covers:

1. The Founder Trap: why success itself becomes the ceiling, and why doubling your leads can actually tank your business
2. Why 66% of Inc. 5000 companies shrink, go under, or sell disadvantageously within 5–8 years of being listed
3. The real definition of marketing — and why even $500M CEOs don't know how to create, capture, and nurture demand
4. Why 100% of all buying decisions will be made before a prospect ever gets on the phone by 2030 (McKinsey and Gartner data)
5. How he built one of the most profitable real estate development companies in his market — with zero prior experience — by working from a book and writing down contractor names off trucks
6. The hospital wake-up call that nearly killed him in his 20s and forced him to stop believing hard work alone was the answer
7. Return on Time (ROT) — the metric that separates real business owners from high-paid employees
8. Why AI is just an accelerator — and why context and strategic thinking are the real competitive moat
9. How to use AI as a virtual board of directors, legal bot, and deal analyzer for real estate investments
10. Why Google's organic traffic dropped 60% in 2025 — and what that means for every investor's marketing plan

This episode is for:

1. Real estate investors and operators stuck between $1M and $10M who feel maxed out
2. Entrepreneurs running a business that can't survive without them
3. Anyone who wants to understand how to use AI strategically — not just to write emails

🔗 Learn more: https://predictableprofits.com

🔗 Build systems for your investing business: https://realdealcrew.com

#EntrepreneurMindset #BusinessGrowth #RealEstateInvesting #ScalingBusiness #PredictableProfits #FounderTrap #AIForBusiness #RealDealChat #BusinessSystems #PassiveIncome

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

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Tim Street reverse-engineered the entire FSBO process into a 7-day blueprint — and his sellers get 102% of list price while saving $30K or more.

In this episode of RealDealChat, Jack Hoss sits down with Tim Street, Marine-turned-real estate agent-turned-FSBO educator, to break down one of the most misunderstood niches in real estate.

Tim covers:

1. Why 90%+ of FSBOs fail — and why the ones that succeed still sell for 11% less than agent-listed homes
2. The 3-phase system: Prep & Protect, Price & Promote, Sell & Secure
3. Strategic underpricing — how Tim achieved a 102.3% list-to-sold ratio by creating competition
4. The "chaos in the driveway" open house strategy that forces buyers to write offers on their steering wheels
5. Why a pre-listing inspection is the single most powerful move a FSBO can make before going live
6. The "truth package" that takes all negotiating ammo away from buyers
7. His 90-day sell guarantee — and the operational safeguard behind it
8. Why he quit the listing game cold after watching a retired couple get lied to for a $500K promise on a $400K house
9. How he uses Claude for narrative script writing and ChatGPT for operations
10. His custom Hemingway-inspired GPT that writes listing descriptions buyers actually read
11. Why 24 touches across 3 platforms is the real follow-up standard — not 6

This episode is for:

1. Real estate investors who want to understand the FSBO seller mindset
2. Homeowners tired of paying 3–6% commissions
3. Agents who want to stop losing listings to overpriced competitors
4. Anyone building a follow-up system around a skeptical, DIY-first audience

🔗 Get Tim's Investor Power Pack: https://foolprooffsbo.com/investors 🔗 Take the FSBO temperament quiz: https://foolprooffsbo.com/quiz

#FSBO #ForSaleByOwner #RealEstateInvesting #HomeSelling #RealDealChat #RealEstateTips #HouseSelling #InvestorMindset #RealEstateAgent #HomeBuying

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

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Dru Wischhover breaks down what title insurance actually covers, the fraud patterns targeting investors, and what kills deals at the closing table.

In this episode of RealDealChat, Jack Hoss sits down with Dru Wischhover, owner of a boutique title company and development firm, to pull back the curtain on one of the most misunderstood parts of real estate investing — title insurance.

Dru covers:

1. The difference between an owner's policy and a lender's policy — and why investors often skip the wrong one
2. Why title insurance covers the past, not the future (and why that matters)
3. Two real fraud cases: a deceased man's signature forged on a deed and a $275K property sold out from under an elderly widow
4. The $500,000 bounced cashier's check that cost Dru clients and a builder relationship
5. Why rush closings are a red flag — and what to look for
6. How assumptions, novations, and stacked assignments actually work from the title side
7. What wholesalers get wrong about disclosure at closing
8. The three things every investor should do to ensure a smooth close
9. Why Dru includes attorney access in his title work — and how that protects investors
10. How he's expanding into Indiana and what the scale-up bottleneck taught him
11. His Heroes Helping Heroes nonprofit launching in 2026

This episode is for:

1. Wholesalers, flippers, and buy-and-hold investors who want to close clean
2. Investors who've been burned by a deal falling apart at the table
3. Anyone who's ever wondered what a title company actually does for them

🔗 Connect with Dru on LinkedIn: search Dru Wischhover (D-R-U)

#TitleInsurance #RealEstateInvesting #RealEstateFraud #WholesaleRealEstate #RealDealChat #ClosingTable #RealEstateTips #HouseFlipping #InvestorMindset #TitleCompany

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

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Daniel McDavid breaks down how to repair your credit in 4–6 months, access up to $50K at 0% interest, and fund your first real estate deal.

In this episode of RealDealChat, Jack Hoss sits down with Daniel McDavid, founder of Move Mountains Funding, to break down one of the most overlooked levers in real estate — credit repair and business funding.

Daniel shares the full journey:

1. How a prayer, an Instagram post, and a $10,000 bet launched his entire business
2. The 4–6 month credit repair timeline (and when it can happen in 30 days)
3. What a trade line is and how it temporarily boosts your credit score to unlock funding
4. How to access $50K–$100K at 0% interest for 12 months through business credit
5. What rental arbitrage is — and why you don't need to own property to cash flow on Airbnb
6. The FCRA rights most consumers don't know they have — and how to use them
7. How to spot a credit repair scam (the Zelle/Cash App red flag)
8. The questions you should be asking any credit repair company before you sign
9. How Daniel's wife went from employee to tax business owner — and the identity shift that made it possible
10. Why Daniel was homeless for five years and how faith drove every financial decision since

This episode is for:

1. New investors who can't get funding because of their credit
2. Anyone who's been denied and doesn't know why
3. Entrepreneurs ready to stop renting their future and start building it
4. Investors who need 0% capital to get their first deal off the ground

🔗 Find Daniel on Instagram: @DanielMcDavid1

🔗 Move Mountains Funding: https://movemountainsfunding.com

#CreditRepair #RealEstateInvesting #BusinessFunding #RentalArbitrage #CreditScore #RealDealChat #FirstRentalProperty #FCRA #ZeroInterest #EntrepreneurMindset

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

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Brandon Cobb went from getting fired to managing $22M in land development — and breaks down exactly how he did it and what almost wiped him out.

In this episode of RealDealChat, Jack Hoss sits down with Brandon Cobb, fund manager and land development coach at Learn Land Development, to unpack one of the most underutilized strategies in real estate investing.

Brandon shares the full journey:

1. How getting fired from medical device sales launched his entrepreneurial path
2. The three phases of land development — entitlement, development, and building
3. His golden rule: don't buy land until all approvals are in place (and the seven-figure lesson he learned the hard way)
4. Why 600+ units in the pipeline doesn't require a massive team
5. How he pivoted from vertical integration to a strategic partner model
6. Why raising private capital is easier than most investors think
7. How he uses custom GPTs for due diligence, zoning reviews, and contract analysis
8. The biohacking habits (cold plunge, no alcohol, Whoop tracking) that fuel his performance
9. His free 8-hour Land Development 101 course at learnlanddevelopment.com

This episode is for:

1. Investors looking to move beyond flipping and rentals
2. Operators with existing cash flow who want to scale into development
3. Anyone curious how to raise private capital for land deals
4. Entrepreneurs tired of being bottlenecked by overhead and employees

🔗 Learn more from Brandon: https://learnlanddevelopment.com

#LandDevelopment #RealEstateInvesting #LandInvesting #CapitalRaising #RealDealChat #EntrepreneurMindset #LandEntitlement #HouseHacking #PrivateMoney #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

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Lane Kawaoka explains passive real estate investing, syndications, and how high-income earners can build wealth without being landlords.

In this episode of RealDealChat, Jack Hoss sits down with Lane Kawaoka from Simple Passive Cashflow to break down how real estate investors can build wealth without managing properties themselves.

Lane specializes in helping high-income professionals transition into passive real estate investing through syndications and private placements.

In this conversation, we cover:

1. What passive real estate investing actually is
2. How syndications work step-by-step
3. Who qualifies as an accredited investor
4. Why high-income earners struggle to scale with rentals
5. The shift from active investing to passive cashflow
6. Risks and misconceptions in syndications
7. How to evaluate deals and operators
8. Why networking and community matter at higher levels

If you’re tired of managing tenants or want to scale beyond single-family rentals, this episode will open your eyes to a different path.

Timestamps:

00:00 – Intro & Meet Lane Kawaoka

01:30 – Lane’s Background & Engineering to Investing

04:00 – What Is Passive Real Estate Investing?

06:45 – Active vs Passive Investing Explained

09:30 – What Is a Syndication?

12:15 – Accredited Investor Breakdown

15:00 – Why High-Income Earners Pivot

18:40 – Risks in Passive Investing

21:30 – Evaluating Deals & Operators

24:15 – Building Wealth Through Networking

27:00 – Common Mistakes Investors Make

30:30 – Final Thoughts

#PassiveIncome #RealEstateInvesting #Syndications #AccreditedInvestor #PassiveRealEstate #CashflowInvesting #MultifamilyInvesting #RealEstatePodcast #InvestorMindset #RealDealChat

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

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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.

Takeaways

1. Real estate investing requires a structured financial approach.
2. A CFO can help track expenses and profits effectively.
3. Detailed financial tracking is crucial for project success.
4. Treating real estate as a business is essential for profitability.
5. Collaboration and communication are key in real estate projects.
6. Understanding profit margins is vital for fix and flippers.
7. Performance-based CFO services can add value to real estate investments.
8. Building strong relationships is critical in business.
9. Financial safety should be a priority for investors.
10. Mistakes in business can be costly, learning from them is essential.

Chapters

00:00 Introduction to CFO Services in Real Estate

01:53 The Importance of Financial Structure in Real Estate

04:35 Managing Multiple Real Estate Projects

06:50 The Role of Technology in Real Estate Accounting

09:29 Treating Real Estate as a Business

12:03 Collaboration Between CFO and Real Estate Investors

20:06 From Mailroom to CFO: A Journey of Growth

23:05 Strategies for Real Estate Investors

26:22 The Importance of Relationships in Business

30:25 Lessons Learned from Mistakes

31:12 Engaging with Entrepreneurs: Open Invitations

34:07 Rapid Fire Insights and Closing Thoughts

40:44 6-sec-outro.mp4

Keywords

real estate investing, CFO services, financial tracking, business strategy, fix and flip, performance-based contracts, investment safety, collaboration, profit margins, business relationships

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

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