The Generations of Wealth

Derek Dombeck

Welcome to “Generations Of Wealth,” where wisdom meets wealth, hosted by the insightful Derek. Derek is not just a podcaster; he’s a seasoned entrepreneur, astute investor, and strategic management expert with a passion for empowering others to build lasting legacies of prosperity. Derek’s journey is a testament to the transformative power of entrepreneurship. Having navigated the dynamic landscapes of business and investing, Derek brings a wealth of experience to the microphone. With each episode, he distills his insights, offering a unique blend of practical advice, inspiring stories, and expert interviews.

  1. -9 H

    How Derek Vickers Built a $20M Mobile Home Park Empire

    📋 Overview In this powerful episode of the Generations of Wealth Podcast, Derek Dombeck sits down with fellow investor and mobile home park mogul Derek Vickers. What began as a door-to-door insurance hustle turned into a multimillion-dollar mobile home park portfolio spanning the Sunbelt. Vickers shares how he went from making $13,000 his first year in sales to now owning 44 parks and 2,100 lots, plus insights into perseverance, communication, and the art of negotiation. The two Dereks dive deep into raising private capital, structuring deals, managing teams, and maintaining integrity in the business — all while emphasizing mindset, accountability, and persistence. 💡 Key Takeaways Perseverance Pays Off: Long-term commitment to consistent action creates exponential results. Negotiation is a Superpower: Communication and mindset matter more than mechanics. Affordable Housing = Recession Resistance: Mobile home parks provide stability and strong demand. Raising Capital with Confidence: You’re not asking for money—you’re offering opportunity. Ownership Mindset: Take accountability for wins and losses to create lasting success. Scaling the Right Way: Team structure, systems, and reinvestment are essential for growth. 🏘️ Relevant Topics Discussed Building a mobile home park empire from scratch Affordable housing trends and market safety Sales psychology and persistence Negotiation frameworks (“No Means Not Yet”) Raising private capital and investor relations Structuring funds and value-add models Managing 40+ parks with regional systems Mindset and personal accountability in entrepreneurship 🎧 Why You Should Listen If you’re an entrepreneur, investor, or anyone tired of quitting too soon, this episode will reignite your belief in what’s possible with consistency, communication, and courage. Learn how Derek Vickers turned adversity into acceleration — and why both Dereks believe persistence and integrity are the foundation of every lasting business. You’ll walk away with real insights you can apply immediately in your next negotiation or deal. ⏱️ Timestamps  00:00–03:00 Intro & The Two Dereks 03:01–10:00 Vickers’ Early Struggles & Door-to-Door Sales Lessons 10:01–16:00 Discovering Real Estate & First Mobile Home Park Deal 16:01–22:00 The Power of Persistence & Sales Mindset 22:01–28:00 Negotiation, Communication & Accountability 28:01–35:00 Scaling to 44 Parks & Managing the Team 35:01–41:00 Raising Capital the Right Way & Investor Mindset 41:01–45:00 Market Outlook, Advice & Final Thoughts #MobileHomeParkInvesting #RealEstateInvesting #AffordableHousing #PassiveIncome #Negotiation #NoMeansNotYet #GenerationsOfWealth #DerekDombeck #DerekVickers #EntrepreneurMindset #FinancialFreedom #PrivateLending #CapitalRaising #RealEstatePodcast #WealthBuilding

    45 min
  2. How to Navigate Lending, Syndications & Industrial Investing in 2025

    10 OCT.

    How to Navigate Lending, Syndications & Industrial Investing in 2025

    Overview In this 37-minute episode, Derek Dombeck sits down with David Hansel, founder of Alpha Funding and Lucerne Capital Partners, for a deep dive into the evolution from single-family flips to commercial and industrial real estate investing. David shares his journey through market cycles, how he built a thriving lending business during the 2008 crash, and how he transitioned into managing over $300M+ in assets through funds and syndications. You’ll gain first-hand insights into hard money lending, fund management, and small-bay industrial investing — with actionable advice for both new and seasoned investors. Key Takeaways How David built a successful hard money lending company during one of the toughest markets. The evolution from retail lending to institutional partnerships and fund structures. Why small-bay industrial properties are a hidden gem in today’s market. How to structure funds and syndications that attract serious capital. What every borrower should know about lender ethics, underwriting, and costs. The mindset shift from flipping $50K homes to handling $50M+ commercial portfolios. Lessons from competitive sports (yes, diving!) that translate directly to business perfection and growth. Relevant Topics  Hard Money Lending vs. Private Money Raising Retail & Institutional Capital Risk Management and Underwriting in Changing Markets Fund Formation, Syndication, and Investor Relations Transitioning from Multifamily to Industrial Real Estate The Rise of Small-Bay Industrial Spaces Building Team Culture & Sustainable Growth Why You Should Listen If you’ve ever wondered how to scale from single deals to managing millions in capital, or how seasoned investors navigate lending, funds, and market shifts — this episode delivers pure gold. David’s perspective combines financial discipline, creative strategy, and practical wisdom every investor needs in today’s climate. ⏱️ Time Stamps  00:00 – Derek’s intro and how David entered real estate 03:00 – Founding Alpha Funding during the 2008 crash 08:30 – Raising capital and managing private investor funds 12:45 – How lending evolved with institutional money 17:00 – Market insights: caution, leverage, and borrower education 22:00 – Transitioning into Lucerne Capital and commercial assets 27:30 – The opportunity in Small-Bay Industrial properties 31:00 – Building funds and syndications the right way 35:00 – Lessons from diving: perfection through small movements 36:30 – Derek’s wrap-up and key mindset takeaways #RealEstateInvesting #HardMoneyLending #PrivateLending #Syndication #FundManagement #IndustrialRealEstate #CommercialInvesting #SmallBayIndustrial #PassiveIncome #GenerationsOfWealth #DerekDombeck #DavidHansel #WealthBuilding #CreativeFinance #EntrepreneurMindset #LiveYourVisionLoveYourLife

    37 min
  3. How to Convert Hotels into Apartments (Safely & Profitably)

    3 OCT.

    How to Convert Hotels into Apartments (Safely & Profitably)

    Overview Derek sits down with Ryan Sudek, CEO of Sage Investment Group, to unpack a repeatable system for converting underperforming hotels/motels into studio apartments—filling an affordability gap while targeting strong returns. They cover market selection, underwriting, construction (sprinklers, sub-panels, kitchens), property management at 100–200 unit scale, and the capital stack behind Sage’s evergreen fund (quarterly distributions, 1031 within the fund, portfolio diversification). Expect practical detail on risk controls (change-of-use permits before closing, value engineering, local code strategy), tenant quality myths (longer average tenancy than market), and why exterior-corridor assets speed construction. The episode closes with goals (10–15 conversions/year, path to 15k units) and how deals actually reach the team (direct-to-seller, lenders, brokers, 60–70 LOIs out at any time). Key Takeaways Niche with low competition: Hotels are valued differently than apartments; conversion unlocks a step-up in value. Tenant reality ≠ myth: Converted assets showed longer average tenancy than national norms, supporting stable cash flow. Market selection > distress alone: Prioritize wage/employment growth; affordable rents still pencil outside “tier-1” cities. Speed & cost levers: Exterior corridors reduce build time (~20% faster); full kitchens + code upgrades (sprinklers, sub-panels) are standard. Operational scale matters: Staff on-site at 100–200 units; centralized construction/asset management drives consistency. Evergreen fund advantages: Diversification, quarterly distributions, 1031 recycling inside the fund, flexible exits. Risk mitigation: Don’t close before change-of-use; collaborate with jurisdictions; tighten cost ranges via repeatability. Deal flow is proactive: Long nurture cycles (18–24 months), direct outreach plus lender/broker channels, many LOIs out concurrently. Why Should You Listen? You want a repeatable adaptive-reuse blueprint that works in multiple states. You’re raising or placing capital and need a portfolio model (evergreen) that smooths cash flow and taxes. You’re curious how to de-risk entitlement & construction on conversions (permits, code, staffing, vendors). Relevant Topics Discussed Hotel vs. apartment valuation spread and where the upside comes from Market/rent comps (Denver studios vs. Carolinas), affordability positioning Unit specs: typical SF, full kitchens, amenities, common-area repurposing Construction/code: sprinklers, electrical sub-panels, energy code, interior vs. exterior corridor Org design: acquisitions, construction mgmt, asset mgmt, on-site staffing Capital: evergreen fund mechanics, 506(b) → 506(c), distributions & 1031 inside the fund Risk controls: purchase terms tied to change-of-use, cost discipline, jurisdiction approach Pipeline & sourcing: off-market, brokers, lender calls, LOI volume and timelines Time Stamps 00:00–03:30 Intro & Ryan’s background; mission and first conversion “light-bulb” moment 03:30–08:00 Why hotels → apartments work; valuation spread; market selection logic 08:00–12:00 Tenant quality myth-busting; occupancy and demand drivers 12:00–16:00 Exterior vs. interior corridors; schedule/cost impact; amenity strategies 16:00–21:00 Construction & code: sprinklers, sub-panels, full kitchens; working with jurisdictions 21:00–26:00 Ops at scale: team structure, on-site staffing, property management cadence 26:00–31:00 Evergreen fund model: diversification, distributions, 1031, 506(b)→506(c) shift 31:00–34:00 Risk mitigation & purchase terms (change-of-use before closing) 34:00–36:00 Goals (10–15/year; path to 15k units), deal sourcing & LOI pipeline; wrap-up #RealEstateInvesting #AdaptiveReuse #HotelToApartment #AffordableHousing #Multifamily #Syndication #EvergreenFund #1031Exchange #ValueAdd #ConstructionManagement #CreativeRealEstate #GenerationsOfWealth #DerekDombeck #SageInvestmentGroup #RyanSudek

    36 min
  4. Syndications vs. Funds (and SEC Traps): Kevin Kim’s Playbook for Raising Capital the Right Way

    26 SEPT.

    Syndications vs. Funds (and SEC Traps): Kevin Kim’s Playbook for Raising Capital the Right Way

    Overview Derek sits down with securities attorney Kevin Kim (Fortra Law) to demystify raising capital for real-estate deals—covering when to use a syndication vs. a fund, realistic startup costs, 506(b) vs. 506(c) advertising rules, what actually happens when regulators come knocking, and how note offerings compare to LP/GP fund structures. They also hit modern twists like series LLC funds, why most beginners should avoid tokenization, and a pragmatic outlook for late-2025 across SFR, small multifamily, and shaky commercial sectors. If you raise money (or plan to), this is your compliance-and-strategy cheat sheet straight from a former regulator. Key Takeaways Syndication ≠ Fund: A syndication is single-asset and generally cheaper; a fund is a multi-asset blind pool with different risks, control, and scalability. Realistic Legal Budgets: Typical legal setup for a basic syndication often ~$15k–$40k depending on complexity; funds cost more. Cutting corners is how sponsors get burned. Don’t Advertise Illegally: Public “I’m raising money” posts can violate securities laws unless you’re properly running Reg D 506(c) with verified accredited investors. Regulator “fishing expeditions” are broad and expensive to answer. Debt vs. Equity Capital: Note offerings are simple but create fixed debt-service and maturity risk; equity/fund structures can offer flexibility and potential tax advantages (e.g., REIT-style considerations) but add complexity. Modern Structures with Caution: Series LLC funds can isolate assets; avoid “investor cherry-picking” designs that smell like SMAs (adviser issues) and beware accounting nightmares. Tokenization is not for beginners. Investor Relations Reality: Small checks often require more hand-holding than large ones; plan your investor base accordingly. Market Outlook (late-2025): Opportunity pockets in SFR/small MF; be cautious on office/retail/industrial; private lending deal flow is uneven but capital availability is strong—only do deals you can underwrite. Why You Should Listen You’ll learn exactly where sponsors get into trouble with the SEC—and how to avoid it. You’ll understand which structure fits your strategy today and how to scale it without legal landmines. You’ll get a practical 2025 lens on which RE sectors deserve your time right now. Relevant Topics Discussed Syndication vs. fund basics • True legal costs • 506(b) vs. 506(c) and advertising • Regulator subpoenas & “bad actor” disqualification risk • Debt funds vs. note programs vs. equity funds • REIT-style considerations • Series LLC funds • Tokenization pitfalls • Crowdfunding realities • Investor ticket-size strategy • 2025 macro outlook for lenders & operators. Time Stamps 00:00 – 02:30 Intro & Kevin’s background (banking → SEC → securities law) 02:31 – 07:30 Syndications vs. funds—what they are, when each fits, realistic setup costs 07:31 – 15:00 Social-media money raising: why casual posts trigger securities violations; 506(b) vs. 506(c) 15:01 – 21:00 What regulators actually do: subpoenas, scope, legal cost, and bad-actor landmines 21:01 – 28:00 Debt (note) programs vs. LP/GP funds—control, leverage, tax angles, and scalability 28:01 – 33:00 Series LLC funds, “cherry-picking” traps, accounting headaches; tokenization—who should not do it 33:01 – 37:30 Crowdfunding lessons; small vs. large investor dynamics; running clean investor relations 37:31 – 40:00 2025 outlook: where opportunity lives; what to avoid; closing advice (“If you can’t underwrite it, don’t do it.”) #RealEstateInvesting #Syndication #PrivateLending #RealEstateFunds #CapitalRaising #SecuritiesLaw #506b #506c #RegD #DebtFunds #EquityFunds #DueDiligence #Underwriting #GenerationsOfWealth #DerekDombeck #KevinKim

    41 min
  5. What Is a Capital Stack? Simple Breakdown for Real Estate Investors

    19 SEPT.

    What Is a Capital Stack? Simple Breakdown for Real Estate Investors

    Overview Derek sits down with multifamily syndicator Randy Langenderfer to unpack his journey from corporate exec to full-time investor and coach. Randy shares the hard-won lessons from starting as an LP, moving into GP roles, structuring deals that align incentives, navigating the interest-rate shock, and where the next opportunities will likely appear. If you want specific questions to vet sponsors, a clear take on 70/30 PREF vs 80/20 “simple stack,” and a realistic read on distressed deals ahead, this one’s for you.  Key Takeaways Sponsor > Property: Track record and character of the sponsorship team ultimately make or break deals—especially when things go sideways. Ask how much true skin they have in the game (beyond rolled acquisition fees).  GOW Podcast - Randy Langenderfer LP → GP Path: Start as an LP to learn, then scale into GP roles via teams with complementary skills; own “a little of a lot” instead of “a lot of a little.”  GOW Podcast - Randy Langenderfer Capital Stack Clarity: Understand tradeoffs between 70/30 with PREF (priority to LPs) vs 80/20 simple split (keeps GPs incentivized in tough markets).  GOW Podcast - Randy Langenderfer Rate Shock Reality: Many 2021–2022 bridge/variable-rate deals are strained; significant loan maturities create distressed opportunities for prepared operators.  GOW Podcast - Randy Langenderfer Taxes That Matter: Depreciation can create paper losses against positive cash flow; learn how allocations flow to LPs/GPs and when REP status matters.  GOW Podcast - Randy Langenderfer Partnerships Need Prenups: Treat partnerships like marriages—define the exit plan upfront to protect relationships and capital.  GOW Podcast - Randy Langenderfer Private Capital Advantage: In choppy markets, aligned private lenders can be more flexible than institutions bound by regulators.  GOW Podcast - Randy Langenderfer Stay in the Game: Cycles change; persistence, due diligence, and conservative structures win over time.    Relevant Topics Discussed Vetting sponsors (character, capital at risk, track record) LP vs GP roles; raising capital ethically PREF returns vs simple splits; incentive alignment Bridge/variable debt risk and refi constraints Bank committees & regulatory pressure vs private lenders Distressed multifamily pipeline and how to access it Depreciation, bonus depreciation, and allocations to LPs/GPs Team building for those “long on energy, short on capital” Partnership structure & exit planning Randy’s “why”: purpose, giving back, staying active Why You Should Listen Actionable vetting questions you can use on your next deal. Clear, BS-free explanations of capital stacks and incentives. Current cycle insights to spot near-term distress and long-term opportunity. Real-world ethics and alignment from someone who’s operated on both LP and GP sides. Time Stamps  0:00 – Intro & Randy’s background: LP beginnings, first GP deal 6:20 – Lessons from early LP investments; why sponsor quality is paramount 11:45 – Transition to GP; building teams and roles that compound strengths 17:00 – “Skin in the game”: what to ask sponsors (fees, at-risk capital) 22:30 – 70/30 PREF vs 80/20 splits: incentives, simplicity, and LP outcomes 31:15 – Market cycle update: rate shock, maturities, and distress window 35:10 – Banks, regulators, and the case for private capital relationships 38:00 – Randy’s “why”: purpose, philanthropy, and staying sharp 39:30 – Wrap & takeaways #RealEstateInvesting #Multifamily #Syndication #PassiveIncome #LPvsGP #CapitalStack #DueDiligence #CommercialRealEstate #DistressedAssets #WealthBuilding #CreativeFinancing #GenerationsOfWealth #DerekDombeck #RandyLangenderfer

    40 min
  6. How to Vet Passive Deals (and Avoid Getting Burned)

    12 SEPT.

    How to Vet Passive Deals (and Avoid Getting Burned)

    Overview Derek sits down with Houston-based investor and capital raiser David Priest to unpack two decades of lessons: surviving the 2008 crash, shifting from transactional work to passive/commercial deals, why operator track record and conservative underwriting beat flashy pro formas, and how to protect yourself in today’s capital stacks (avoid bridge debt, prefer simple structures with LPs directly behind the bank). They also cover buying when others panic, the power of boots-on-the-ground, and a novel principal-protection approach for LPs. Key Takeaways Back the jockey: Prioritize operators with 10–15+ years and full deal cycles completed. Simple capital stacks win: Bank → LPs; be wary of mezzanine debt and complex pref stacks. Bridge debt = hidden risk: Favor long-term, fixed-rate agency loans on MF. Underwrite for durability, not sizzle: Think steady 15–20% targets vs. “home run” bets. Buy when it’s ugly: Cyclical pain can create value—if the fundamentals make sense. Stick to your numbers: Conservative buy boxes outlast hot markets. Market matters & proximity helps: Leverage trusted boots-on-the-ground. Investor protection is evolving: Principal-protection style structures can trade a fee for downside cover. Relevant Topics Discussed Surviving 2008 and the thinning of the herd Transition from mortgages/single-family to syndications Capital stack 101: bank, mezzanine, preferred equity, LPs Bridge vs. fixed agency debt in multifamily Return structures (e.g., 8% pref, equity splits) and principal protection ideas Operator selection, conservative underwriting, and market selection (Texas/Midwest) Collaboration mindset: “Who Not How” Time Stamp Suggested chapter marks 00:00 — Intro & show setup 01:05 — David’s background (Houston, mortgages, resilience) 04:30 — Lessons from 2008; staying when others quit 08:10 — From passive LP to capital raising; mindset shift 12:40 — Failed 90-unit, pivot to raising for proven operators 15:30 — Single-family resilience; sticking to buy boxes 19:20 — Buying when there’s “blood in the streets” 23:10 — Capital stack basics; why mezz/pref can push LPs last 27:15 — Dangers of bridge debt; prefer long-term fixed 31:00 — 8% pref, returns, and principal-protection concept 34:20 — Boots-on-the-ground & market selection 36:20 — What makes David different; collaboration 38:20 — Close & CTA #GenerationsOfWealth #RealEstateInvesting #PassiveIncome #Multifamily #CapitalStack #Syndication #Underwriting #BridgeDebt #TexasRealEstate #OperatorTrackRecord #WhoNotHow #DerekDombeck

    37 min
  7. How to Survive a Real Estate Crash in 2025

    5 SEPT.

    How to Survive a Real Estate Crash in 2025

    Overview Derek sits down with David “Dave” Seymour (A&E’s Flipping Boston) for a blunt, no-fluff masterclass on thriving through market cycles. Dave shares his firefighter-to-investor story, the costly lessons behind refis and 2007, how TV fame and hard-money lending actually work, why control of capital beats “cheap” bank money, and the underwriting discipline needed now. They unpack Florida’s boom-bust dynamics, pivoting plays (from land to pickleball to flex), building real networks (and a strict “no-a**hole policy”), and Dave’s 2025–26 plan: scalable education + cherry-picked commercial deals—grounded in faith, family, and service.  Key Takeaways Cycles reward discipline: It’s not just rates—bad underwriting & speculation break deals. Buy right, model stress, and sleep at night.  Control the capital: Private money and structure > “cheapest bank debt,” because speed & certainty win.  Pivot fast: Markets shift; winners repurpose assets (e.g., land → pickleball concept → flex/industrial).  Scale smart: Bigger isn’t always better—overhead, servicing, and defaults rise nonlinearly.  Invest in accountability: Real mentorship beats “YouTube University.” Pay to shortcut mistakes.  Network is net worth: Podcasts and partnerships multiply deal flow—enforce a no-jerks rule.  2025–26 outlook: Massive reset = opportunity for trained buyers; focus on shelter demand (MF, student/elderly, sober living).  Relevant Topics Discussed 2003–2008 lessons; refi traps & ARMs A&E Flipping Boston behind-the-scenes: ethics over drama Hard-money lending vs. non-QM shutdowns during COVID Syndication, waterfalls, accredited investors (Freedom Venture/Legacy Alliance) Conservative underwriting & deal triage Florida (Cape Coral/Fort Myers) cycle patterns: residential ↔ commercial Land strategies & adaptive reuse (pickleball → flex) Education stack: financial literacy, Inflation Nation (book/film), masterclasses Faith, family, and service as long-term drivers  Time Stamps  00:00 Intro: why networks matter 01:15 Dave’s path: firefighter → investor; 2007 wake-up call  05:20 Seminars, paying for accountability, and early wins/mistakes  09:30 Flipping Boston: getting the show, partner dynamics, and TV realities  14:20 Ethics on camera: refusing “manufactured drama”  16:30 Hard-money business model; COVID’s hit vs. private-capital shops  20:45 Control of capital → syndication & fund structures 24:10 It wasn’t rates—it was shaky underwriting and management  27:00 Florida focus: overbuilds, ghost listings, and where value still hides  30:10 Land pivots: pickleball plan, competition shock, flex solution  33:00 Scaling pitfalls: servicing, defaults, and team capacity 35:10 Mentors vs. “YouTube U”: compressing the learning curve  37:30 Network building & the “no-a**hole policy” 39:20 2025–26: Legacy Alliance, Inflation Nation, and cherry-picking deals  42:10 Faith & family: the real why 44:10 Action steps + call to share #RealEstateInvesting #DavidSeymour #DerekDombeck #FlippingBoston #CommercialRealEstate #Multifamily #HardMoneyLending #RealEstateTips #Syndication #Underwriting #MarketCycles #Networking #FinancialLiteracy #Entrepreneurship #LegacyAlliance

    46 min
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À propos

Welcome to “Generations Of Wealth,” where wisdom meets wealth, hosted by the insightful Derek. Derek is not just a podcaster; he’s a seasoned entrepreneur, astute investor, and strategic management expert with a passion for empowering others to build lasting legacies of prosperity. Derek’s journey is a testament to the transformative power of entrepreneurship. Having navigated the dynamic landscapes of business and investing, Derek brings a wealth of experience to the microphone. With each episode, he distills his insights, offering a unique blend of practical advice, inspiring stories, and expert interviews.