🧾 Summary

Fred Moskowitz shares how the volatility of the tech industry led him to seek alternative income streams and ultimately discover mortgage note investing. Instead of owning properties and dealing with tenants, Fred focuses on owning the debt—collecting payments as the lender rather than the borrower.

Together, Derek and Fred walk through the fundamentals of note investing, including buying performing notes, using partials to deploy smaller amounts of capital, understanding foreclosure timelines, evaluating borrower risk, and navigating state-specific laws. They also discuss taxation realities and why self-directed IRAs and Roth IRAs can be powerful vehicles for note investors.

This episode demystifies note investing and shows how it can fit into both active and passive investment strategies.

⭐ Key Takeaways

• Note investing means owning the debt, not the property — you become the bank.

• Performing notes offer steady, lower-risk cash flow compared to distressed notes.

• Non-performing notes and workouts offer higher returns but require more time and expertise.

• Partials allow investors to start with less capital and increase velocity of money.

• Notes are purchased at a discount, increasing yield beyond the borrower's interest rate.

• State foreclosure laws matter — timelines and costs impact pricing and risk.

• Equity position, borrower history, and location drive note value.

• Institutional notes offer consistency and cleaner documentation.

• Note investing creates taxable income, unlike rental depreciation strategies.

• Self-directed IRAs and Roth IRAs can dramatically improve returns when used properly.

• Time availability determines strategy — passive funds vs active note portfolios.

📚 Relevant Topics Discussed

• What note investing is and how it works

• Becoming the bank vs owning real estate

• Performing vs non-performing notes

• Partial note investing explained

• Pricing notes and risk factors

• Borrower behavior and loan performance

• Foreclosure laws and state-by-state differences

• Institutional vs private seller-financed notes

• Yield expectations and cost of capital

• Taxation of notes vs rental properties

• Using self-directed IRAs and Roth IRAs

• Passive vs active note investing strategies

🎧 Why Should You Listen?

Listen to this episode if you:

• Want passive cash flow without tenants or toilets

• Are curious about owning notes instead of properties

• Want to diversify beyond traditional real estate

• Have retirement funds sitting idle

• Want predictable income streams

• Are exploring lower-volatility investment options

• Want to understand risk before buying notes

• Are deciding between active or passive investing

• Want a beginner-friendly breakdown of note investing

This episode is ideal for real estate investors, lenders, retirement-account holders, and anyone looking to add stable income to their portfolio.

⏱️ Time Stamps

• 00:00 – 03:15 | Introduction & Fred's background

• 03:16 – 07:40 | Why note investing exists & becoming the bank

• 07:41 – 12:30 | Performing vs non-performing notes

• 12:31 – 16:50 | Partial notes & yield examples

• 16:51 – 21:30 | Pricing notes & risk factors

• 21:31 – 25:40 | Foreclosure laws & legal considerations

• 25:41 – 29:45 | Taxes, IRAs, and Roth strategies

• 29:46 – 32:30 | Passive vs active note investing

• 32:31 – 34:00 | Getting started & final advice

#NoteInvesting #GenerationsOfWealth #PassiveIncome #BeTheBank #MortgageNotes #RealEstateInvesting #AlternativeInvestments #CashFlow #RothIRAInvesting #SelfDirectedIRA #FredMoskowitz #DerekDombeck

📄 Summary

Derek interviews Jeff, his personal VA based in the Philippines, to answer the questions business owners ask most but rarely hear honest answers to. Jeff shares his background, experience working with U.S. clients, and how his role expanded from simple tasks into podcast management, CRM oversight, marketing funnels, real estate support, and operations.

The episode dives deep into the human side of virtual teams: trust, communication, initiative, accountability, and mutual respect. Derek explains why he doesn't track screens or micromanage, while Jeff explains why treating VAs like family—not disposable labor—creates loyalty, productivity, and long-term success.

They also discuss the realities of working across time zones, internet instability, cultural differences, cost of living, fair compensation, and why honesty matters on both sides. The episode closes with a powerful reminder: if you want to scale your business, you must learn to scale relationships, not just tasks.

⭐ Key Takeaways

• A business that scales cannot remain a one-person operation

• Hiring a VA is about trust and leadership, not surveillance

• Great VAs grow with the business — they don't just complete tasks

• Personality fit matters as much as technical skill

• Direct-hire vs. agency VAs both have pros and cons

• Clear expectations upfront prevent long-term frustration

• Time zone differences can be an advantage when structured properly

• Treating VAs as disposable leads to high turnover and poor results

• When clients succeed, VAs succeed — it's a shared outcome

• Long-term teams are built on respect, honesty, and growth

💬 Relevant Topics Discussed

• When a business is "ready" for a VA

• Where to find virtual assistants

• Part-time vs. full-time VA roles

• Hourly rates and cost of living realities

• Agency VAs vs. direct hires

• Training vs. hiring experienced talent

• Trust, accountability, and work ethic

• Internet, power outages, and contingency planning

• Time zone alignment and productivity

• Building culture with remote teams

🎧 Why Should You Listen?

Listen to this episode if you:

• Are overwhelmed running everything yourself

• Have hired a VA before and it didn't work

• Want to scale but don't know where to start

• Struggle with delegation or trust

• Want honest insight from both sides of the VA relationship

• Care about building a sustainable, people-first business

This episode doesn't just tell you how to hire a VA — it shows you how to lead one.

#VirtualAssistants #BusinessScaling #RemoteTeams #EntrepreneurLife #GenerationsOfWealth #Leadership #HiringTips #OnlineBusiness #TeamBuilding #BusinessGrowth #WorkFromAnywhere #VACommunity #RealEstateEntrepreneur #PodcastBehindTheScenes

📘 Overview

This episode of the Generations of Wealth Podcast explores one of the most misunderstood yet powerful tools available to investors: self-directed retirement accounts. Derek is joined by Henry Yoshida, founder and CEO of Rocket Dollar, a technology-enabled self-directed IRA custodian.

Henry shares why most investors even sophisticated, high-net-worth ones—don't understand how self-directed IRAs work, why traditional custodians frustrate investors, and how real estate and alternative assets are quietly reshaping retirement investing. The conversation dives into control, velocity of capital, prohibited transactions, required minimum distributions, and why real estate inside retirement accounts is growing fast.

This episode reframes retirement money not as "locked-up capital," but as deployable investment fuel when used correctly.

⭐ Key Takeaways

• Most investors don't know self-directed IRAs exist, even sophisticated ones.

• Traditional custodians slow deals down, causing missed closings and frustration.

• IRA-owned entities restore control and speed, allowing investors to wire funds themselves.

• Custodians should not judge deal quality, only IRA eligibility.

• Prohibited transactions are a real risk, especially for hands-on investors.

• Real estate inside IRAs is growing rapidly, especially passive and private credit deals.

• Required Minimum Distributions (RMDs) explain much of government retirement policy.

• Stocks and bonds no longer diversify each other—real estate fills that gap.

• Investors want control and understanding, not just higher returns.

• Private and alternative investments may surpass public markets within 10 years.

💬 Relevant Topics Discussed

• Self-directed IRAs explained simply

• Why most custodians frustrate real estate investors

• IRA-owned entities vs. checkbook control IRAs

• Velocity of capital and missed real estate closings

• Prohibited transactions and compliance risks

• Required Minimum Distributions (RMDs)

• Why retirement capital is underutilized

• Passive real estate, private credit, and syndications

• Crypto and other alternative investments in IRAs

• Control vs. convenience in investing

🎧 Why Should You Listen?

Listen to this episode if you:

• Have old 401(k)s or IRAs sitting idle

• Raise capital from IRA investors

• Want faster, cleaner real estate closings

• Are frustrated with traditional IRA custodians

• Want to invest retirement funds outside Wall Street

• Care about long-term tax efficiency and control

• Want to understand retirement money at a deeper level

This conversation gives investors clarity, confidence, and a practical framework for using retirement accounts as part of a real estate wealth strategy.

⏱️ Time Stamps

00:00 – 02:30 Episode intro, why IRAs and alternative investing matter

02:31 – 06:15 Henry Yoshida's background & Merrill Lynch years

06:16 – 10:45 Why most investors don't know about self-directed IRAs

10:46 – 15:30 Problems with traditional IRA custodians & slow closings

15:31 – 20:20 Rocket Dollar model & IRA-owned entities explained

20:21 – 25:10 Velocity of capital, wiring funds, and real estate timing

25:11 – 29:45 Prohibited transactions & real-world investor mistakes

29:46 – 34:20 Required Minimum Distributions (RMDs) & government incentives

34:21 – 38:40 Real estate, private credit & alternative investments inside IRAs

38:41 – 41:40 Future of private investing vs. public markets

41:41 – 43:27 Final insights, where to find Rocket Dollar & closing remarks

#SelfDirectedIRA #RealEstateInvesting #AlternativeInvestments #GenerationsOfWealth #RetirementStrategy #PassiveIncome #PrivateCapital #FinancialFreedom #WealthBuilding #IRAInvesting #RealEstateWealth #TaxAdvantaged #PrivateEquity #InvestorEducation

🧾 Summary

Alan Underwood opens up about losing family members, walking away from a multimillion-dollar business, and rebuilding his life from the ground up. While many chase growth at all costs, Alan emphasizes that success without alignment leads to burnout, emptiness, and regret.

This conversation goes far beyond business tactics. Derek and Alan dive into vision, gratitude, identity, legacy, and mindset—discussing why most people unknowingly live someone else's dream, why scaling doesn't always equal freedom, and how intentional reflection can realign your life and business.

The episode challenges listeners to stop chasing numbers and start designing a life that actually feels meaningful.

⭐ Key Takeaways

• Success and happiness are not the same thing — financial wins can still leave you empty.

• Vision must come before scale — growth without alignment creates burnout.

• Identity drives results — you will never outperform who you believe you are.

• Legacy is about impact, not income — people remember how you showed up, not your net worth.

• Gratitude changes perspective instantly — most "problems" are really perspective issues.

• Self-love is foundational — learning to love and forgive yourself unlocks growth.

• Regular reflection is essential — vision should evolve intentionally, not accidentally.

• Celebrating wins matters — unacknowledged success leads to emotional exhaustion.

• What you consume shapes who you become — protect your mental inputs.

• Transformation requires action — clarity without movement changes nothing.

📚 Relevant Topics Discussed

• Vision vs. achievement

• Identity and mindset transformation

• Burnout and entrepreneurial pressure

• Coaching and personal growth

• Gratitude as a daily practice

• Legacy vs. income

• Scaling businesses without losing yourself

• Self-love and forgiveness

• Perspective and mental health

• Designing a life aligned with purpose

• Celebrating wins intentionally

• Protecting mental inputs and focus

🎧 Why Should You Listen?

You should listen to this episode if you:

• Feel successful on paper but unfulfilled in life

• Are questioning whether your business supports your vision

• Struggle with burnout, pressure, or constant "more"

• Want clarity on purpose beyond money

• Are building wealth but don't want to lose yourself doing it

• Believe success should feel better than it does

• Want to live with intention, gratitude, and alignment

This episode is raw, reflective, and deeply human—perfect for entrepreneurs, investors, and leaders who want more than just financial success.

⏱️ Time Stamps

• 00:00 – 03:30 | Introduction & Alan's background

• 03:31 – 07:45 | Loss, burnout, and walking away from success

• 07:46 – 12:30 | Coaching, identity, and discovering purpose

• 12:31 – 17:40 | Vision vs. scaling and fulfillment

• 17:41 – 22:30 | Legacy, gratitude, and perspective

• 22:31 – 27:20 | Identity, habits, and mental conditioning

• 27:21 – 31:50 | Self-love, forgiveness, and transformation

• 31:51 – 36:18 | Action, alignment, and living your vision

#GenerationsOfWealth #LiveYourVision #EntrepreneurMindset #VisionDrivenLife #PersonalGrowth #LegacyOverIncome #HighPerformance #MindsetMatters #BusinessWithPurpose #GratitudePractice #WealthWithMeaning #AlanUnderwood #DerekDombeck

📘 Overview

This episode of the Generations of Wealth Podcast takes a deep dive into one of the most misunderstood and risky areas of real estate investing: raising capital legally. Derek Dombeck is joined by SEC and syndication attorney Nic McGrue, founder of Polymath Legal, who has helped clients raise and acquire over $2.5 billion in assets.

Together, they break down how syndications really work, the most common (and dangerous) mistakes investors make when raising money, how the SEC views joint ventures, social media marketing, finder's fees, and what investors must have in place to stay compliant while building generational wealth.

⭐ Key Takeaways

• Most capital-raising mistakes come from ignorance, not bad intent — but the penalties can be severe.

• Joint ventures are often misused and do not replace proper securities exemptions.

• Social media capital-raising is risky when returns, guarantees, or deal specifics are shared publicly.

• Syndications require specific legal documents, including operating agreements, PPMs, and SEC filings.

• PPMs protect operators as much as investors by clearly disclosing risks.

• 506(b) vs. 506(c) matters — pre-existing relationships and accreditation rules change everything.

• Second-position capital is extremely risky, especially in distressed markets.

• Market downturns expose weak operators and reward disciplined, compliant ones.

💬 Relevant Topics Discussed

• What legally defines a real estate syndication

• Syndications vs. funds — where investor money really goes

• Equity vs. debt structures and investor risk

• Common SEC violations investors don't realize they're committing

• Why posting returns on social media is dangerous

• PPMs, operating agreements, and SEC filings explained

• Accredited vs. sophisticated investors

• Finder's fees and why commissions are a legal landmine

• Market cycles, distressed assets, and future opportunities

🎧 Why Should You Listen?

Listen to this episode if you:

• Plan to raise private money or capital for deals

• Want to avoid costly legal mistakes in syndications

• Are investing passively and want to understand your risks

• Use (or plan to use) social media to attract investors

• Want clarity on SEC rules without legal jargon

• Care about long-term credibility, trust, and generational wealth

This episode could literally save you from a lawsuit, an SEC investigation, or losing investor trust.

#RealEstateSyndication #RaisingCapital #PrivateMoney #GenerationsOfWealth #SECCompliance #PassiveInvesting #RealEstateLaw #AccreditedInvestor #WealthBuilding #CapitalRaising #InvestorEducation #RealEstatePodcast

📘 Overview

In this powerful 38-minute conversation, Derek and Shawn Moore dive deep into the real story behind a 25-year real estate journey filled with massive wins, devastating losses, personal challenges, and ultimate reinvention. Shawn shares how he survived losing everything twice, rebuilt from scratch, discovered the power of the short-term rental (STR) asset class, and shifted his business — and life — toward building generational impact.

The episode blends real estate strategy, creative financing, mindset, failure, family, and the importance of understanding that STRs aren't just properties — they're experience-driven businesses. It's raw, honest, emotional, and full of actionable lessons for any investor navigating changing markets.

⭐ Key Takeaways

• STRs are an experience business, not just real estate — hospitality matters more than granite countertops.

• COVID-era performance was a blip, not a baseline; supply has now caught up, exposing poor underwriting.

• Demand for STRs is still strong, growing ~11% annually, but only well-run properties win today.

• Creative deal structuring is essential, not optional — lease options, subject-to, and seller financing saved Shawn early on and still create opportunities today.

• Losing everything can be a blessing when it forces humility, growth, and better decision-making.

• True legacy isn't assets — it's self-reliance, responsibility, and teaching your kids how to build their own path.

• Market downturns create opportunity for those who know how to underwrite, negotiate, and structure deals.

💬 Relevant Topics Discussed

• Shawn's real estate start in 2000 and the rise/fall of fix-and-flip success

• Losing everything twice — and rebuilding with purpose

• Emotional challenges of infertility and family-building

• Why STR investors failed after the COVID boom

• How to correctly underwrite STR deals today

• Supply vs. demand and the new realities of the STR market

• Using creative financing to acquire deals when you're not bankable

• Legacy, mindset, humility, and entrepreneurship

🎧 Why Should You Listen?

This episode is for anyone who:

• Wants the real, unfiltered truth about long-term success in real estate

• Needs perspective on overcoming setbacks, both personal and financial

• Is considering investing in short-term rentals

• Wants to understand how to operate STRs profitably in today's market

• Values open, honest conversations about failure, family, legacy, and resilience

• Wants to sharpen negotiation and creative financing skills with real-world stories

Shawn brings decades of wisdom — the kind you only earn by getting knocked down and choosing to stand back up.

⏱️ Time Stamps

00:00 – 02:30 Derek sets the stage & importance of creative deal structuring 02:31 – 07:00 Shawn's background & early years in real estate (2000–2006) 07:01 – 12:00 High-end development, big money… then losing everything 12:01 – 17:30 Rebuilding in 2009: selling homes, working with investors 17:31 – 23:00 The one property he didn't lose — his first STR 23:01 – 28:00 Family, infertility struggles & redefining legacy 28:01 – 32:30 The STR market today: supply, demand & post-COVID realities 32:31 – 35:30 Creative financing: lease options, subject-to & seller carries 35:31 – 38:00 Steak, bourbon, and final wisdom

#RealEstatePodcast #ShortTermRentals #STRInvesting #VacationRentals #GenerationsOfWealth #MindsetMatters #RealEstateInvesting #CreativeFinancing #NegotiationSkills #FinancialFreedom #RealEstateJourney #OvercomingFailure #LegacyBuilding #WealthMindset #EntrepreneurLife

📄 Summary

In this powerful conversation, Jens shares how he left a long IT career, discovered real estate in his 40s, and grew from small four-unit buildings to thousands of multifamily and industrial square footage. He breaks down current market conditions, the pressure syndicators are feeling, and where he sees opportunities going forward.

The heart of the episode centers on personal transformation how mindset coaching helped him overcome fear, redefine success, and build a life around purpose instead of pressure. Derek and Jens discuss vision, fulfillment, the danger of chasing "someday," and why entrepreneurs must build businesses that support the life they want—not the other way around.

⭐ Key Takeaways

• It's never too late to start — Jens began investing in his mid-40s and has since built an impressive portfolio.

• Mindset is the real engine of success — limiting beliefs, fear, and lack of clarity stop more people than lack of money.

• Current multifamily markets are stressed — insurance, taxes, repairs, and interest rates are crushing many deals.

• Industrial and flex space are strong alternatives — stable tenants, triple-net structures, and strong demand.

• Build a business around your life vision — not the other way around.

• Coaching created Jens's breakthrough — clarity + confidence = action.

• Young entrepreneurs must bring value first — skills, time, creativity, and effort can open big doors.

• Happiness isn't found in achievement — it's cultivated daily through mindset and intentional living.

📚 Relevant Topics Discussed

• Leaving a W-2 career later in life

• Growing from small multifamily to syndications

• Market pressure: taxes, insurance, interest rates

• Industrial & flex space investing

• Raising private vs institutional capital

• Mindset transformation & limiting beliefs

• Vision-driven entrepreneurship

• Coaching and personal development

• Financial education gaps in America

• How young people can start without money

• Building partnerships by adding value

• Aligning business with personal life goals

🎧 Why Should You Listen?

Listen to this episode if you want to understand:

• How to reinvent your life at any age

• How to break free from a W-2 mindset

• What real estate strategies are working right now

• How to overcome fear and step into entrepreneurship

• The mindset shifts that create true freedom

• Why vision matters more than units, deals, or cash flow

• How to bring value and attract mentors or partners

• The difference between building wealth and building fulfillment

This episode blends tactical real estate wisdom with deep personal growth insights—making it valuable for new investors, seasoned entrepreneurs, and anyone looking to design a more intentional life.

⏱️ Time Stamps

• 00:00 – 01:20 | Derek introduces Jens and the theme of late-career reinvention

• 01:21 – 06:40 | Jens's journey: Denmark → London → U.S. → IT career

• 06:41 – 11:55 | Discovering real estate in his mid-40s & early multifamily deals

• 11:56 – 16:45 | 2,500 units, GP/LP roles & national market insights

• 16:46 – 21:10 | Market pressures: insurance, taxes, interest rates

• 21:11 – 24:50 | Opportunities in industrial and flex space

• 24:51 – 29:20 | Mindset, coaching, and shifting from technician to entrepreneur

• 29:21 – 32:00 | Vision, fulfillment & building a life-aligned business

• 32:01 – 33:52 | Advice to young investors & Jens's five-year vision

#RealEstatePodcast #GenerationsOfWealth #MindsetMatters #RealEstateInvesting #EntrepreneurMindset #MultifamilyInvesting #IndustrialRealEstate #Syndication #PersonalGrowth #WealthBuilding #LifeByDesign #FinancialFreedom #CoachingForSuccess #DerekDombeck #JensNielsen

📌 Overview

Derek and Pascal explore the world of passive investing, due diligence, long-term wealth strategy, and how everyday investors can model the same approach that major institutions use. Pascal explains how he vetted deals across 23+ investments, the role of understanding inevitabilities, and how his unique experience in venture capital shaped his investment philosophy. They also dive into macro trends affecting real estate, from industrial growth and medical facilities to low-income housing and why Airbnb might be a dangerous play.

Key Takeaways

• Investing without a thesis is gambling — you must know why a deal will win over the long term.

• Fear holds people back — especially when managing family money; process and due diligence remove that fear.

• Venture capital is extremely high-risk — 9/10 investments fail and 80% of funds don't return capital.

• Think in 10-year inevitabilities — crypto adoption, automation, robotaxis, AI, decentralization.

• Institutional-style investing is accessible now thanks to democratized platforms.

• Real estate plays Pascal is bullish on: industrial, triple-net, medical/assisted living, mobile home parks, and low-income housing.

• Most investors lose by buying at the top—don't follow the herd.

• Your best investments will be the ones people told you were stupid.

Relevant Topics Discussed

• How institutional investors perform due diligence

• Comparing stocks, VC, and real estate risk profiles

• Democratization of passive investing platforms

• How to build a diversified cash-flowing portfolio

• Long-term economic inevitabilities

• The "silver tsunami" and aging population trends

• Why Airbnb and multifamily may be in trouble

• Building an investment thesis with confidence

• Mistakes that cause investors to lose money

Why Should You Listen?

If you want to understand how wealthy families and major institutions build generational wealth, this episode gives you the roadmap. Pascal breaks down investing in a way that is simple, relatable, and actionable. Whether you're just getting started or already investing six figures, this conversation helps you think bigger, avoid common traps, and make smarter decisions with your money.

Time Stamps

00:00 – Welcome & Guest Introduction 01:05 – Pascal's background: Germany → Florida → Colorado 02:00 – Selling his startup & joining Techstars VC fund 03:30 – Managing his mother's inheritance after his father passed 05:15 – Learning institutional due diligence 07:10 – Differences between stocks, VC, and real estate 09:20 – Vetting operators vs. vetting your own deals 11:00 – Investing based on 10-year inevitabilities 13:40 – Venture capital explained for real estate investors 16:00 – High-risk, high-reward dynamics of VC 18:15 – Democratizing passive investing platforms 20:00 – How to start investing like Pascal (step-by-step) 22:15 – Derek & Pascal on mentorship and avoiding mistakes 23:40 – Outlook for 2026 and beyond 26:10 – Big-picture trends: crypto, AI, EVs 28:05 – Real estate areas Pascal is bullish on 30:20 – The #1 mistake investors make 32:30 – Final thoughts, resources, and sign-off

#GenerationsOfWealth #PassiveInvesting #AlternativeInvestments #RealEstateInvesting #VentureCapital #FinancialFreedom #WealthStrategy #CryptoInvesting #IndustrialRealEstate #LongTermInvesting #MoneyMindset #InvestorTips

*]:pointer-events-auto [content-visibility:auto] supports-[content-visibility:auto]:[contain-intrinsic-size:auto_100lvh] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1" data-turn-id= "b0951ee5-de29-4230-a55a-052a53880e61" data-testid= "conversation-turn-44" data-scroll-anchor="true" data-turn= "assistant"> Overview

This episode maps a practical path from a professional W-2 to operator and capital raiser. Savannah explains how she identified accessible capital, learned hard lessons from early single-family turns, and pivoted to multifamily for scale. She details how to educate investors (especially healthcare peers), structure compliant raises, and maintain discipline during due diligence—even walking away when a deal breaks. Finally, she outlines an assisted-living strategy that leverages clinical operations, demographic tailwinds, and systemized team roles with her spouse.

Key Takeaways

• Start with accessible capital (e.g., primary-home equity) to get into your first meaningful deal.

• Single-family teaches fast but scales slowly; multifamily systems and cash flow create durability.

• Relationship-first 506(b) syndications can attract peers from your industry; education is the flywheel.

• Underwrite conservatively; be ready to terminate and pivot investor capital when the thesis breaks.

• Clear roles (acquisitions/asset management vs. investor relations/marketing) accelerate execution.

• Assisted living can compound operational advantage for healthcare operators and investors.

Relevant Topics Discussed

• W-2 to investor/operator progression

• Underwriting discipline and market selection (tertiary markets, occupancy resilience)

• 506(b) basics, investor education, and communication cadence

• Deal structures, splits, and using bank/agency debt with investor equity

• Due-diligence checkpoints and kill-criteria

• Assisted-living strategy: licensing, staffing, private-pay dynamics, and risk control

Why Should You Listen

If you're a busy professional aiming to scale beyond single-family or invest alongside an experienced operator, this episode offers a repeatable blueprint: where to find capital, how to structure and communicate deals, how to protect investors with disciplined underwriting, and how to leverage industry expertise—especially in healthcare—to create a true edge.

Time Stamps

• 00:00 — From bedside nursing to first rentals

• 02:30 — Using home equity and early single-family lessons

• 06:00 — Pivot to multifamily and first syndications

• 10:30 — Underwriting during uncertainty; selecting resilient markets

• 15:00 — Investor education, 506(b) relationships, and communication

• 19:30 — Deal structures, splits, and debt choices

• 24:00 — Due-diligence discipline and when to walk away

• 28:30 — Assisted-living thesis and operational edge

• 33:00 — Working with a spouse, roles, and next steps

#RealEstateInvesting #Multifamily #Syndications #AssistedLiving #Underwriting #CapitalRaising #PassiveInvesting #CreativeFinance #CashFlow #DerekDombeck

📘 Overview

In this episode, Derek sits down with self-storage powerhouse Jacob Vanderslice, who went from flipping houses in the mid-2000s to owning 41 self-storage facilities, 21,000 units, and 3.5M+ sq ft across 15 states.

Jacob breaks down: • How he survived multiple market cycles • Why self-storage is still strong despite economic uncertainty • How to raise capital the right way • What investors are doing wrong in today's market • Why transparency and discipline matter now more than ever

This is a straight-talking conversation packed with real-world lessons on scaling, managing risk, surviving downturns, and building a durable real-estate business.

⭐ Key Takeaways

• Cycles Create Wealth — Experienced investors make their biggest gains during market dislocations, not booms.

• Self-Storage Thrives on Mobility — Demand is tied to people moving. As movement returns, storage demand will rise.

• The Biggest Issue in 2024–2025: Debt — Rising rates, floating loans, and debt maturities are crushing poorly structured deals.

• Transparency Wins Investors — Deliver bad news faster than good news. Investors value honesty over perfection.

• Don't Force Deals — In tight markets, the winners are the ones who wait for great deals, not "make the numbers work."

• Operational Excellence Matters — In today's environment, execution and downside protection matter more than projections.

• Take Action — The worst thing a new investor can do is nothing. There's no perfect deal, only well-structured ones.

📌 Relevant Topics Discussed

• Evolution from flips → development → commercial → self-storage

• Market cycles, interest rates, and macro pressures

• Investor relations, reporting, capital raising challenges

• Overpaying, rookie mistakes, and "selling the dream" deals

• Operational headaches (break-ins, staff, overhead, U-Haul damages)

• Sustainable business building vs. chasing scale

• Finding off-market deals vs. broker relationships

• Structuring investor equity, preferred returns, and K-1 benefits

• Risk management and avoiding unsustainable models

• Why action beats perfection for new investors

🎧 Why You Should Listen

This episode is for you if:

• You're an investor who wants to survive — and thrive — in a shifting market.

• You want to understand the real economics behind self-storage.

• You're raising capital (or want to) and need to understand what LPs fear most right now.

• You've lost deals, money, momentum, or confidence — and want a roadmap forward.

• You want unfiltered truth from two investors who have been through the fire and came out stronger.

⏱️ Time Stamp

00:00 – Intro & Derek opens the show 01:10 – Jacob's background & early real estate lessons 03:30 – Transition into self-storage & scaling nationwide 05:45 – Market challenges in 2024–2025 07:20 – Macro trends, demand softening & economic uncertainty 10:50 – Why storage demand dropped 13:05 – Derek on "thinning of the herd" in real estate 15:40 – Investor mistakes & overpriced deals 18:20 – Raising capital in today's environment 19:40 – LP pain: equity wipes, capital calls, paused distributions 22:05 – Transparency & communicating with investors 26:15 – How Jacob sources deals (off-market + brokers) 28:20 – Ideal deal size & investment parameters 29:50 – How investor structures work (pref, equity, K-1s) 31:30 – Managing 427 investors & reporting systems 33:10 – Team size & operational setup 36:20 – Not forcing deals & staying disciplined 38:00 – Hard money lending parallels & risk cycles 39:20 – Reality of storage operations (not passive) 40:20 – Jacob's advice: take action, take smart risks 41:30 – Political uncertainty & market psychology 43:45 – Derek's final send-off

📄 Summary

Derek and guest Jacob Vanderslice dive deep into the mindset and mechanics behind building a durable real-estate business — specifically self-storage. Jacob shares how he went from fighting fires to building a multi-state storage empire by surviving market cycles, raising capital responsibly, and developing systems that scale.

They discuss the current market environment, rising rates, cracks in the economy, deal flow challenges, overpriced assets, and investor fear. Jacob explains why transparency and delivering bad news quickly is critical when managing investor capital, and why operational excellence matters more now than ever.

The conversation also covers sourcing off-market deals, building long-term investor trust, managing a large operations team, navigating overhead, and avoiding the pitfalls that wipe out rookies. The episode ends with timeless advice: take action, take smart risks, and don't wait for the perfect deal.

#RealEstateInvesting #SelfStorageInvesting #CommercialRealEstate #PassiveIncome #WealthBuilding #MarketCycles #RealEstateTips #InvestorMindset #CapitalRaising #RealEstatePodcast #GenerationsOfWealth #DerekDombeck