The Generations of Wealth

Derek Dombeck
  • 5.0 (3)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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. 2D AGO

    How AI Is Fixing the Biggest Problem in Real Estate Transactions

    What if the biggest deal-killer in real estate wasn't price… but uncertainty? In this episode, Derek sits down with Jeremy Henley, founder of The Quick Fix, to discuss how artificial intelligence is solving one of the most frustrating parts of real estate transactions: the home inspection process. Jeremy combines years of real estate investing experience with a deep background in predictive modeling and AI to eliminate uncertainty around inspection reports, contractor pricing, and repair negotiations. If you've ever lost a deal because of an inspection, struggled to get contractors to show up, or dealt with buyer anxiety during due diligence this episode is for you.   Derek and Jeremy dive into: Why inspection uncertainty kills deals How AI can standardize repair pricing The friction between agents and contractors How to negotiate repairs properly Why certainty closes more transactions The future of inspections and AI in real estate The shrinking pool of skilled tradespeople How technology is changing transaction speed This episode blends real estate investing, contractor management, AI, negotiation strategy, and industry trends into one powerful conversation.   ⭐ Key Takeaways Inspection reports create uncertainty — uncertainty kills deals. AI can analyze inspection reports and generate executable repair quotes. Most contractor friction comes from low-probability "shopping" jobs. Negotiation should focus on unknown safety issues — not cosmetic items. Standardizing repair pricing builds trust between buyers and sellers. AI won't replace contractors — but it will streamline the process. The future of real estate includes fewer agents with higher productivity. Skilled trades will remain in high demand for decades. Certainty closes more deals than emotion. 📚 Relevant Topics Discussed AI in real estate Home inspection negotiations Repair credits vs. repair requests Contractor marketplace models FHA/VA appraisal conditions Risk reduction in transactions Remote property management Standardization of repair pricing Predictive modeling & machine learning Due diligence strategy The future of skilled trades Scaling real estate operations with tech 🎧 Why Should You Listen? Listen if you: ✅ Have ever lost a deal due to inspection issues ✅ Struggle to get contractors to respond quickly ✅ Want more certainty in repair negotiations ✅ Flip houses and hate the due diligence phase ✅ Are curious about AI in real estate ✅ Work with buyers who experience repair anxiety ✅ Want to future-proof your investing business This conversation hits directly at a problem every serious investor has experienced. ⏱️ Time Stamps  00:00 – 04:00 Jeremy's background: Farm life to tech & real estate 04:01 – 10:00 The inspection problem & uncertainty in deals 10:01 – 18:00 How AI reads inspection reports & builds repair quotes 18:01 – 25:00 Negotiation strategy: What buyers should and shouldn't ask for 25:01 – 32:00 Contractor friction & standardizing pricing 32:01 – 38:00 Appraisal repair conditions & lender challenges 38:01 – 44:00 Future of AI in real estate & inspection trends 44:01 – 48:00+ Industry outlook, skilled trades & final insights #GenerationsOfWealth #RealEstateInvesting #AIInRealEstate #HomeInspection #PropertyFlipping #RealEstateTechnology #InvestorMindset #RealEstateTips #ContractorLife #DueDiligence #JeremyHenley #DerekDombeck

    40 min
  2. You Might Also Like: Las Culturistas with Matt Rogers and Bowen Yang

    2D AGO · BONUS

    You Might Also Like: Las Culturistas with Matt Rogers and Bowen Yang

    Introducing "ChuckleHut 3000 On The Corner Of Butt And Ass" (w/ Sarah Sherman) from Las Culturistas with Matt Rogers and Bowen Yang. Follow the show: Las Culturistas with Matt Rogers and Bowen Yang There's a tonnage of laughter on this one as Sarah Sherman is back! Her special, Live + In The Flesh is streaming on HBO Max, so the child has popped by a get blackout drunk on about four sips of Martini and get through almost a whole a hand of topics. You will have several Big Osaka Laughs and be Sent Boots as a result of your listening experience.  See omnystudio.com/listener for privacy information. DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

  3. FEB 13

    The Psychology of Wealth: Avoiding the Mistakes That Destroy Fortunes

    📘 Overview In this episode of the Generations of Wealth Podcast, Derek sits down with wealth advisor Jonathan Blau, a seasoned financial planner with decades of experience helping affluent families grow and preserve wealth. Rather than focusing on picking investments, Jonathan explains why behavior — not intelligence — is the biggest driver of financial success or failure. The conversation dives into behavioral finance, investor psychology, inflation risk, volatility myths, generational wealth, and why many investors sabotage themselves without realizing it. Jonathan challenges traditional industry thinking, offering a fresh perspective on risk, forecasting, emotional decision-making, and long-term investing. This episode is less about tactics — and more about mastering the mindset required to build lasting wealth.   ⭐ Key Takeaways Behavioral mistakes destroy more wealth than bad investments Overconfidence increases as wealth grows Volatility is temporary — inflation is permanent Forecasting markets is largely ineffective Surprise is the biggest trigger for investor panic Long-term investing requires emotional discipline True diversification protects families and heirs Speculation is not the same as investing Generational wealth is built through consistency Happiness is not tied to financial accumulation   💬 Relevant Topics Discussed Behavioral finance explained Defining true wealth Inflation vs volatility risk Long-term equity performance Sequence of return risk Investor psychology during downturns Why forecasting fails Crypto vs traditional investing Generational wealth strategies Wealth and happiness   🎧 Why Should You Listen? Listen to this episode if you: Want to become a smarter, more disciplined investor Struggle with emotional decision-making during market shifts Believe wealth is about more than just money Want to protect your family financially Are curious about the psychology behind successful investing Want perspective outside the real estate echo chamber This conversation will challenge how you think — not just about investing, but about wealth itself.   ⏱️ Time Stamps  00:00 – 03:00 Intro & Jonathan's background 03:01 – 07:00 Defining true wealth 07:01 – 12:00 Behavioral finance & investor mistakes 12:01 – 17:30 Inflation vs volatility explained 17:31 – 22:00 Retirement strategy & risk management 22:01 – 26:30 Forecasting myths & market unpredictability 26:31 – 30:30 Equities, diversification & long-term growth 30:31 – 34:30 Crypto vs investing 34:31 – 38:00 Wealth, happiness & final insights   #GenerationsOfWealth #WealthBuilding #BehavioralFinance #InvestorMindset #FinancialFreedom #SmartInvesting #LongTermWealth #MoneyPsychology #GenerationalWealth #InvestingTips #FinancialEducation #WealthStrategy #PassiveInvesting #BuildWealth

    39 min

  4. FEB 5

    Think Like an Investor: Market Cycles, Smart Deals & Building Real Wealth

    🧾 Summary Joel Kraut's journey began on Wall Street, where he spent over two decades trading through major economic cycles — including the historic crash of 1987. After transitioning into real estate, he rapidly scaled a large portfolio using leverage before the 2008 crash wiped out millions and forced a hard reset. Instead of quitting, Joel rebuilt smarter — focusing on disciplined investing, strong partnerships, and long-term strategy rather than speculation. Together, Derek and Joel dive into: Why success is about solving problems, not chasing properties How market cycles create opportunity for prepared investors The power of partnerships and scaling with the right people Why communication builds trust with lenders How relationship capital can outperform financial capital The importance of multiple exit strategies Using modern tools like AI to stay competitive The episode ultimately shifts beyond real estate — challenging listeners to design a life aligned with freedom, purpose, and fulfillment. ⭐ Key Takeaways Success in real estate starts with thinking differently. The best deals come from solving real human problems. Market cycles reward disciplined investors — not speculators. Relationship capital is often more valuable than cash. Partnerships can accelerate growth while reducing risk. Communication builds long-term trust with lenders and partners. Always have multiple exit strategies before buying. Leverage technology and AI or risk falling behind. Execution beats intelligence — action creates opportunity. True wealth is flexibility, freedom, and time — not just money. 📚 Relevant Topics Discussed Market cycles & investor psychology Recovering after financial loss Creative deal structuring Seller financing & partnerships Scaling across multiple markets Relationship-based investing Risk management Private lending dynamics Communication with investors AI in real estate Opportunity cost & capital velocity Building generational wealth Designing a life around freedom 🎧 Why Should You Listen? Watch this episode if you want to: ✅ Learn how seasoned investors think during uncertain markets ✅ Avoid costly mistakes newer investors make ✅ Understand how relationships drive opportunity ✅ Gain confidence navigating market shifts ✅ Learn how to scale responsibly ✅ Build wealth without sacrificing your life ✅ Think like a professional investor — not a gambler This conversation is packed with practical wisdom, mindset shifts, and timeless investing principles. ⏱️ Time Stamps  00:00 – 04:00 Introduction & Joel's background 04:01 – 09:00 Wall Street lessons & surviving major market crashes 09:01 – 14:00 Scaling into real estate and losing millions in the housing collapse 14:01 – 18:30 Rebuilding smarter & learning disciplined investing 18:31 – 23:30 Market cycles, perspective, and where opportunity lives 23:31 – 28:30 Finding deals by solving problems 28:31 – 33:30 Creative structuring & real-world deal examples 33:31 – 38:00 Relationship capital and partnership strategy 38:01 – 42:30 Risk management, lenders, and communication 42:31 – 46:30 Leveraging AI, technology, and staying relevant 46:31 – 50:00 Building a life you love vs. just surviving 50:01 – 52:00 Final wisdom & closing thoughts #RealEstateInvesting #GenerationsOfWealth #InvestorMindset #WealthBuilding #MarketCycles #PassiveIncome #Entrepreneurship #FinancialFreedom #PrivateMoney #RealEstatePodcast #BusinessGrowth #RelationshipCapital #JoelKraut #DerekDombeck

    53 min

  5. JAN 30

    How to Win in Any Market Using Creative Real Estate

    📘 Overview In this milestone 100th episode of the Generations of Wealth Podcast, Derek Dombeck welcomes back long-time friend, mentor, and creative real estate expert Chris Prefontaine. Chris shares his journey from losing everything in the 2008 crash to building one of the most respected creative real estate education platforms in the country. Together, Derek and Chris dive deep into creative deal structuring, the 3 Paydays strategy, market shifts, mindset, ethics, and why today's market presents massive opportunity for investors who know how to operate outside traditional financing. This episode blends experience, humor, strategy, and real-world insight—making it one of the most valuable conversations in the series.   ⭐ Key Takeaways Creative financing thrives in uncertain markets — especially when banks tighten lending. The 3 Paydays model creates income upfront, monthly cash flow, and long-term backend profits. You don't need perfect credit or bank loans to build wealth in real estate. Seller financing and subject-to deals are powerful tools when done ethically. Market shifts create opportunity, not fear, for prepared investors. Doing deals the right way protects buyers and sellers long-term. Mindset and consistency matter more than tactics. The best investors adapt instead of quitting. Relationships outperform transactions every time. Success comes from action—not overthinking. 📚 Relevant Topics Discussed Creative real estate investing Seller financing & subject-to deals The 3 Paydays strategy Market cycles and opportunity Ethical real estate practices Coaching and mentorship Building long-term wealth Mindset for investors Avoiding common real estate pitfalls Creating win-win deals Scaling without banks Community-based learning 🎧 Why Should You Listen? You should listen to this episode if you: Want to invest without relying on banks Are curious about creative real estate strategies Want to understand how to thrive in uncertain markets Feel stuck or overwhelmed by traditional investing Want to learn from someone who rebuilt after failure Value ethics, long-term thinking, and sustainable wealth Want real-world insight, not theory Are serious about building generational wealth This episode is equal parts strategy, mindset, and real-life experience—perfect for new investors and seasoned pros alike.   ⏱️ Time Stamps 00:00 – 03:15 Introduction, Episode 100 milestone & why this conversation matters 03:16 – 07:00 Chris's background, early career, and lessons from the 2008 crash 07:01 – 11:00 How the 3 Paydays strategy was created and why it works 11:01 – 15:00 Creative real estate explained: buying on terms vs traditional financing 15:01 – 18:45 Why today's market creates massive opportunity for creative investors 18:46 – 22:30 Ethics in real estate, protecting sellers & buyers, and doing deals right 22:31 – 26:15 Subject-to deals, seller financing & avoiding common mistakes 26:16 – 30:00 Mindset, coaching, and why most investors stall before success 30:01 – 33:30 Building long-term wealth, community, and relationships 33:31 – 37:00 Final insights, Episode 100 reflections & closing message   #GenerationsOfWealth #CreativeRealEstate #3Paydays #RealEstateInvesting #SellerFinancing #SubjectTo #WealthBuilding #MindsetMatters #RealEstateEducation #ChrisPrefontaine #DerekDombeck #FinancialFreedom

    38 min

  6. JAN 23

    The Smarter Way to Be a Landlord: Property Management, Sustainability & Scale

    📄 Summary David Holman shares how his real estate journey began after realizing traditional employment wouldn't provide the lifestyle or financial security he wanted for his growing family. Starting with single-family rentals, David gradually scaled into mixed-use and small commercial properties, learning firsthand the importance of management, tenant relations, and long-term thinking. A major theme of the conversation is treating tenants as assets, not liabilities. David explains how maintaining properties, investing in energy efficiency, and creating livable spaces leads to better tenants, fewer vacancies, and higher long-term returns. He also walks through his experience with mixed-use buildings, triple-net leases, and why smaller commercial units can often outperform large single-tenant properties. Derek and David discuss the realities of historic buildings, the risks of deferred maintenance, and why many investors underestimate renovation and compliance costs. The episode wraps with a deep dive into environmental upgrades — insulation, heat pumps, energy efficiency, and grants — showing how smart improvements can significantly increase NOI while also improving tenant quality of life. ⭐ Key Takeaways Your best asset isn't the property — it's the tenant Good management reduces turnover, repairs, and stress Mixed-use and small commercial properties can outperform residential Triple-net leases reduce expenses but increase vacancy risk Energy efficiency upgrades create long-term ROI Insulation and air sealing are some of the highest-return improvements Heat pumps can dramatically lower operating costs Government grants and incentives are often underutilized Real estate success is built on relationships, not shortcuts Long-term thinking beats short-term profit chasing 💬 Relevant Topics Discussed Transitioning from residential to mixed-use real estate Tenant relationships and retention Commercial vs residential investing Triple-net leases explained Property management philosophy Energy efficiency and sustainability Heat pumps, insulation, and operating costs Environmental upgrades with real ROI Grants, tax incentives, and hidden opportunities Scaling responsibly as a landlord 🎧 Why Should You Listen? You should listen to this episode if you: Own or want to own rental properties Want better tenants and fewer headaches Are curious about mixed-use or small commercial investing Care about long-term value over short-term gains Want to improve cash flow without raising rents Believe real estate should be run like a business — not a gamble This episode is a reminder that the best investors play the long game and that treating people well is often the most profitable strategy of all.   ⏱️ Time Stamps (38 Minutes) 00:00 – 03:00 Intro & David's background 03:01 – 07:30 From nonprofit work to real estate investing 07:31 – 12:00 First properties & early lessons learned 12:01 – 16:30 Tenant relationships & property mindset 16:31 – 21:00 Mixed-use buildings & commercial investing 21:01 – 25:30 Triple-net leases & risk vs reward 25:31 – 30:00 Environmental upgrades & efficiency 30:01 – 34:00 Grants, insulation & heat pumps 34:01 – 38:00 Long-term vision & final takeaways   #GenerationsOfWealth#RealEstateInvesting#LandlordLife #PropertyManagement#RealEstatePodcast #WealthBuilding#RentalProperties#CommercialRealEstate#SustainableInvesting#EnergyEfficiency#PassiveIncome #RealEstateEducation#LongTermWealth #SmartInvesting

    39 min

  7. JAN 16

    Note Investing Made Simple: Becoming the Bank

    🧾 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

    34 min

  8. JAN 9

    Behind the Business: How to Build a Real Team with Virtual Assistants

    📄 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

    35 min
See All (104)

5
out of 5
3 Ratings

About

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.

Information