Overview:

In this episode, Derek brings in Tracy Dombeck—his wife and longtime bookkeeper—to shine a light on a topic often overlooked by entrepreneurs: bookkeeping. They cover everything from basic financial hygiene to handling complex real estate deal structures like flips, rentals, subject-to transactions, and lease options. Packed with practical advice, this is a must-listen for real estate investors who want to protect their profits, avoid audits, and keep the IRS off their back.

📌 Why Should You Listen?

• You're a real estate investor (or planning to be one).

• You’ve been “winging it” with your books or relying on QuickBooks guesses.

• You want to avoid common tax-time disasters.

• You’re doing creative deals and don’t know how to track them.

• You’re unsure whether to hire a VA, bookkeeper, or CPA—and when.

✅ Key Takeaways

1. Bookkeeping isn’t optional. Bad habits now lead to huge penalties later.

2. Separate your business and personal finances. No co-mingling!

3. Track EVERYTHING. Small receipts matter and can reduce your tax burden.

4. Know when a 1099 worker is really an employee. Get this wrong = audit & penalties.

5. Rental vs. flip properties must be categorized differently.

6. Subject-to deals & lease options need special bookkeeping treatment.

7. Hiring cheap bookkeepers can cost you more in cleanups later.

8. Review your Profit & Loss and Balance Sheet monthly.

9. W-9s, 1099s, and correct classifications are critical.

10. TrustPoint Bookkeeping offers flexible, experienced help nationwide.

🧠 Relevant Topics Discussed

• Bookkeeping for real estate investors

• Flip vs. rental property accounting

• Subject-to financing & lease option tracking

• Payroll, W-9s, and contractor vs. employee

• Sales tax, use tax, and IRS compliance

• Hiring bookkeepers vs. VAs

• Setting up separate business accounts

• Cost expectations for professional bookkeeping

⏱️ Timestamps (approximate) Time Topic 00:00–02:00 Introduction & why bookkeeping matters 02:00–06:00 Common mistakes investors make with receipts and records 06:00–09:00 Business vs. personal finances—separate everything! 09:00–13:00 Employees vs. 1099 contractors—don’t get caught 13:00–15:00 Sales tax misconceptions and receipt management 15:00–18:00 Payroll basics and why it’s not as scary as it sounds 18:00–20:30 Interest reporting and W-9/1099 rules 20:30–23:00 Categorizing rentals vs. flips—common investor errors 23:00–25:00 Handling subject-to deals and closing statements 25:00–27:30 Lease options and how to track option fees correctly 27:30–29:30 Dangers of hiring untrained VAs for bookkeeping 29:30–31:00 What bookkeeping services cost and what to expect 31:00–32:00 Final advice and how to contact TrustPoint Bookkeeping

 

#RealEstateInvesting   #BookkeepingTips   #GenerationsOfWealth   #TracyDombeck   #TrustPointBookkeeping   #CreativeRealEstate   #TaxStrategies   #SubjectToDeals   #LeaseOptions   #REInvestorTips   #KnowYourNumbers   #ProfitAndLoss   #RealEstateFinance  

📋 Episode Summary:

In this powerhouse episode, real estate mogul and entrepreneur Ashley Wilson joins Derek Dombeck for a candid, unscripted conversation that dives deep into multifamily real estate, the true value of in-person networking, and her mission to bring transparency and innovation to the conference world. Ashley unpacks her journey from clinical research to managing over $160M in real estate assets, co-founding Apartment Addicts, and launching the platform Conference Connect. The discussion also tackles the current multifamily market, negotiation dynamics, personal accountability, and the future of live events. Whether you're a new investor, a seasoned operator, or someone passionate about personal growth—this episode hits on all cylinders.

💡 Key Takeaways:

1. From Corporate to Real Estate Titan: Ashley transitioned from clinical research to real estate, scaling across flipping, rentals, and large multifamily acquisitions.

2. Conference Connect's Purpose: Addressing inefficiencies in the conference industry, the platform empowers attendees, vendors, and organizers to connect meaningfully and transparently.

3. Power of In-Person Events: Strategic, high-value connections often emerge in informal moments—like dinners or hallway chats—not through Zoom or YouTube alone.

4. Multifamily Market Outlook: Ashley shares why the market's current turbulence is far from over, and why regulation, oversight, and education matter more than ever.

5. Women in Real Estate: Her book The Only Woman in the Room uplifts female voices in the space and helps break barriers in a traditionally male-dominated industry.

6. Negotiation Is Human: Face-to-face communication adds context, energy, and emotional intelligence—crucial in a world trending digital.

7. Own Your Mistakes: Both Derek and Ashley reinforce that accountability is a superpower in investing and in life.

🎧 Why You Should Listen:

• You're in or considering commercial/multifamily real estate.

• You’ve ever been burned by flashy “gurus” and want the real, no-BS truth.

• You want to learn how conferences can be leveraged more strategically.

• You’re a woman navigating a male-dominated industry (or want to support those who are).

• You believe in the power of networking, relationship capital, and personal accountability.

• You want to level up your negotiation game with emotional intelligence and presence.

⏱️ Time Stamps (Total Length: 47:16)

• 00:00 – 03:00 – Football banter and intros

• 03:00 – 07:30 – Ashley’s journey into real estate

• 07:30 – 13:00 – What is Conference Connect and why it matters

• 13:00 – 18:00 – The event industry, vetting speakers, and vendor visibility

• 18:00 – 24:00 – Why in-person events are irreplaceable

• 24:00 – 28:30 – Negotiation in-person vs. online

• 28:30 – 33:00 – Real-life negotiation wins and emotional influence

• 33:00 – 37:30 – The Only Woman in the Room – the story behind the book

• 37:30 – 41:30 – Ashley’s market outlook on multifamily real estate

• 41:30 – 46:00 – Accountability, vetting operators, and learning from failure

• 46:00 – 47:16 – Final thoughts, resources, and where to follow Ashley

🔖 Hashtags:

#RealEstateInvesting #MultifamilyRealEstate #AshleyWilson #ConferenceConnect #WomenInRealEstate #NetworkingMatters #InPersonEvents #RealEstateCoaching #TheOnlyWomanInTheRoom #NegotiationSkills #DerekDombeck #GenerationsOfWealth #RealEstateEducation #InvestorMindset

Summary:

In this insightful episode of the Generations of Wealth Show, host Derek Dombeck welcomes Brett Swarts, founder of Capital Gains Tax Solutions, to challenge the traditional 1031 exchange and unveil a more flexible, investor-friendly strategy: the Deferred Sales Trust (DST). Brett shares how DST empowers investors to defer capital gains taxes, diversify investments, and most importantly—reclaim their time and freedom.

Through powerful stories of clients who exchanged active property management for peace of mind and increased cash flow, Brett makes the case that building wealth should never come at the cost of your family or lifestyle. If you’ve built up significant equity and are looking for a better way out, this episode is your roadmap.

✨ Key Takeaways:

• 1031 exchanges are outdated: Investors often feel forced to reinvest quickly, overpay, or take on excessive debt—often resulting in poor outcomes.

• Deferred Sales Trusts offer control and flexibility: Investors can defer capital gains, customize income streams, and diversify into real estate, stocks, Bitcoin, or their own ventures.

• DST = Passive income with freedom: The DST structure allows investors to regain their time while still growing their wealth.

• Real examples drive the point home: Brett shares real stories of families who deferred millions in taxes, boosted cash flow, and prioritized time with loved ones.

• It’s about impact, not just income: DST planning helps investors live aligned with their vision, values, and mission.

🎧 Why Should You Listen?

• You’ve ever felt boxed in by 1031 exchange deadlines or rules.

• You want to exit real estate or a business but dread the tax bill.

• You value both wealth building and time freedom.

• You're an entrepreneur, real estate investor, or high-net-worth individual looking to maximize your exit strategy.

⏱️ Time Stamps:

• 0:00 – Welcome & Brett’s background: From real estate to tax solutions

• 4:38 – How the 2008 crash shaped Brett’s mission

• 7:20 – Why 1031 exchanges often fail investors

• 10:42 – The Deferred Sales Trust explained: The Netflix to 1031’s Blockbuster

• 14:15 – Real-life case study: From 15 units to financial freedom

• 20:50 – Step-by-step mechanics of the DST

• 26:40 – Who qualifies for this strategy

• 29:45 – Can you adjust or access your funds early? Yes!

• 33:10 – Passive or active? You choose how involved you want to be

• 36:00 – How control and oversight work in a DST

• 39:00 – Succession plan: What if something happens to Brett?

#CapitalGainsTax #DeferredSalesTrust #1031ExchangeAlternative  #PassiveIncome #RealEstateInvesting #WealthStrategy #FinancialFreedom  #TaxStrategy #ExitPlanning #GenerationsOfWealth #DerekDombeck #BrettSwarts

In this episode of the Generations of Wealth Podcast, we sit down with Yakov Smart, a leading expert in investor attraction, to uncover the strategies that help real estate investors and entrepreneurs secure capital, build meaningful connections, and grow their businesses. Yakov shares his proven methods for leveraging LinkedIn and other platforms to attract high-net-worth investors without cold calls or outdated tactics.

🔑 Key Topics Covered: ✔️ How to attract high-net-worth investors ✔️ The power of LinkedIn for capital raising ✔️ Avoiding common mistakes when seeking investment ✔️ The psychology of investor engagement ✔️ Why networking is more than just making connections

📌 Why You Should Listen: If you're looking to scale your real estate business, secure more funding, or improve your networking skills, this episode is packed with insights that can help you raise capital faster and more efficiently. Yakov’s expertise can help you refine your investor outreach strategy and stand out in a crowded market.

🚀 Want to connect with Yakov? Visit [insert website or social links] to learn more about his investor attraction strategies!

🎙️ Subscribe & Stay Connected 🔔 Hit the bell icon to stay updated on future episodes!

#InvestorAttraction #RealEstateInvesting #RaisingCapital #LinkedInMarketing #EntrepreneurMindset

Key Takeaways:

• The Shift in Investor Outreach – Why traditional methods fail and how to pivot.

• LinkedIn as a Game Changer – How Yakov uses LinkedIn to attract investors.

• Common Mistakes in Raising Capital – What to avoid when seeking investments.

• Psychological Triggers for Investors – Understanding how investors think.

• Networking That Converts – How to build lasting and profitable relationships.

Time Stamps:

⏱ 0:00 - Introduction to Yakov Smart ⏱ 2:30 - Yakov’s journey into investor attraction ⏱ 6:15 - Why traditional capital raising doesn’t work anymore ⏱ 10:40 - How LinkedIn helps investors build authority ⏱ 15:20 - The three biggest mistakes people make in investor outreach ⏱ 20:45 - The psychology behind high-net-worth investors ⏱ 26:30 - How to structure an effective investor attraction funnel ⏱ 33:00 - Real-life success stories from Yakov’s clients ⏱ 37:45 - Final thoughts & where to connect with Yakov

#InvestorAttraction #RealEstateInvesting #RaisingCapital #LinkedInMarketing #NetworkingTips #WealthBuilding #EntrepreneurMindset #BusinessGrowth #CapitalRaising #InvestorPsychology

Summary

In this episode of the Generations of Wealth Podcast, host Derek Dombeck speaks with Pat Martin, a seasoned real estate investor and coach. Pat shares his journey from wrestling and coaching to ministry work and eventually becoming a successful real estate investor specializing in pre-foreclosures and distressed properties. They discuss ethical investing, foreclosure strategies, and how to acquire properties for as little as $10. The conversation also covers controversial real estate practices, including equity stripping, sub-to deals, and the Remick rule, and how to do business the right way with integrity.

Key Takeaways

✅ Pat Martin’s Background – From coaching and ministry work to 20+ years in real estate investing. ✅ Ethical Real Estate Investing – Importance of doing business legally, morally, and ethically. ✅ Equity Stripping Lawsuit – Discussion on a recent case in Arizona where investors were accused of unethical foreclosure practices. ✅ Foreclosure Investing Done Right – Strategies for acquiring properties ethically and legally. ✅ Buying Properties for $10 – How Pat structures deals with distressed homeowners. ✅ The Remick Rule Strategy – How banks use IRS loopholes, and how investors can leverage it to eliminate liens. ✅ Sub-to & Assignments – The risks and ethical concerns of subject-to transactions and assignments. ✅ Lead Generation – Proven methods to find pre-foreclosures and motivated sellers. ✅ Pat’s Pre-Foreclosure Course – Exclusive $1,500 discount for podcast listeners.

Why Should You Listen?

🎯 If you're in real estate – Learn real foreclosure strategies without unethical tactics. 💡 If you're new to investing – Avoid scams, bad deals, and risky practices. ⚖ If ethics matter to you – Understand the right way to invest in distressed properties. 📢 If you want actionable insights – Pat shares real-life examples and step-by-step deal breakdowns.

Time Stamps

📌 0:00 - 5:00 – Introduction & Pat’s Background 📌 5:01 - 15:00 – Transition into Real Estate & Pre-Foreclosures 📌 15:01 - 30:00 – Ethical vs. Unethical Investing & Arizona Lawsuit Discussion 📌 30:01 - 45:00 – The Right Way to Handle Foreclosures & Sub-to Concerns 📌 45:01 - 1:00:00 – Buying Houses for $10 & The Remick Rule Strategy 📌 1:00:01 - 1:11:00 – Final Thoughts & Pat’s Course Discount Offer

 

#RealEstate #Foreclosures #Investing #EthicalInvesting #RealEstatePodcast #WealthBuilding #PreForeclosures #RealEstateInvestor #PassiveIncome #GenerationsOfWealth

📌 Summary

In this episode, Melissa Hoyer, a financial planner and wealth coach at The Wealth Conservancy, discusses the challenges of inherited wealth and how to successfully manage and sustain generational wealth. She explains how many inheritors feel overwhelmed, the different stages of inherited wealth, and how financial coaching helps heirs transition from uncertainty to confidence. The conversation also explores estate planning, avoiding family disputes over money, and teaching financial responsibility to future generations.

📍 Key Takeaways

✅ Stages of Inherited Wealth – Many heirs experience denial, confusion, and overwhelm before taking control of their finances. ✅ Wealth Can Disappear in 3 Generations – Without proper planning, wealth is often squandered, as reflected in the saying, "Shirt sleeves to shirt sleeves in three generations." ✅ Estate Planning is Essential – Having a clear plan and transparent communication prevents family disputes and ensures a smooth wealth transfer. ✅ Teach Kids Financial Responsibility Early – Introducing money management skills and fostering a strong work ethic helps children appreciate wealth. ✅ Time is the Ultimate Wealth – True wealth isn’t just money; it’s about time, relationships, and life experiences.

🎙️ Why Should You Listen?

🔹 Learn how to prepare your heirs for wealth and avoid financial mismanagement. 🔹 Understand the common pitfalls of inherited wealth and how to navigate them. 🔹 Get expert insights on estate planning, wealth coaching, and financial literacy for kids. 🔹 Hear personal stories and practical tips on building a lasting financial legacy.

⏳ Time Stamps (31:22 Episode Length)

📌 [00:00 – 03:00] Introduction & Melissa Hoyer’s background in financial coaching 📌 [03:01 – 10:00] The stages of inherited wealth & why most heirs struggle 📌 [10:01 – 16:00] The importance of wealth coaching & how to avoid squandering wealth 📌 [16:01 – 22:00] Estate planning tips – preventing family disputes over inheritance 📌 [22:01 – 27:00] Teaching financial literacy to kids & passing down more than just money 📌 [27:01 – 31:22] Final thoughts & how to build generational wealth beyond finances

#GenerationalWealth #FinancialFreedom #WealthManagement #EstatePlanning #MoneyMatters #FinancialLiteracy #WealthBuilding #LegacyPlanning #FinanceTips #SuccessMindset

In this powerful episode of the Generations of Wealth Podcast, Kathy Tucarro shares her extraordinary journey—from being a nurse to losing everything and becoming homeless, to rebuilding her life and landing a job as a heavy equipment operator for one of the world’s largest mining companies.

Kathy opens up about her darkest moments, overcoming trauma, and rediscovering self-worth. She shares how a single moment of realization led her to transform her life and why believing in yourself is the key to breaking barriers. Today, she’s not only an author, speaker, and philanthropist but also a voice of hope and resilience for anyone facing adversity.

If you’ve ever felt stuck, faced challenges, or needed inspiration to push forward, this is an episode you don’t want to miss.

Key Takeaways:

✅ Your past doesn’t define your future – No matter how low you feel, change is possible. ✅ Mindset is everything – The way you think about yourself impacts your ability to grow. ✅ Opportunities exist if you seek them – Kathy’s career shift came from a willingness to try something new. ✅ Overcoming adversity makes you stronger – Every challenge is a stepping stone to a better future. ✅ Giving back creates impact – Kathy’s work with the homeless and charity initiatives shows how one person can make a difference.

Why Should You Watch This Episode?

🚀 Real-life transformation story – From homelessness to success. 💡 Powerful mindset shifts – Learn how to push past limitations. 🔥 Breaking gender barriers – Kathy succeeded in a male-dominated industry. 💪 Inspiration for overcoming adversity – Whether personal or professional, this episode will ignite your motivation.

Time Stamps 

⏳ [00:00] - Introduction 🎙 Host Derek Dombeck introduces Kathy Tucarro and her incredible journey.

⏳ [02:15] - From Nurse to Homeless 📉 Kathy shares how she lost everything and ended up on the streets.

⏳ [06:40] - The Turning Point ⚡ A moment with a homeless man made Kathy realize she had to change her life.

⏳ [12:10] - Finding Confidence Through Heavy Equipment Operation 🚜 How she went from laughing at the idea to making it her career.

⏳ [18:30] - Breaking Gender Barriers in a Male-Dominated Industry 💪 Overcoming doubts and proving she belongs in mining.

⏳ [24:00] - Giving Back: Philanthropy & Mentorship ❤️ Kathy’s charity work, Operation Hydration, and work boot donation program.

⏳ [28:45] - Lessons for Entrepreneurs & Business Owners 📈 The importance of mindset shifts when facing challenges.

⏳ [32:30] - Kathy’s Podcast & Final Thoughts 🎤 Learn about her show "Women Road Warriors" and where to follow her journey.

#GenerationsOfWealth #Podcast #KathyTucarro #OvercomingAdversity #DreamBig #MindsetMatters #SuccessStory #WomenInBusiness #Motivation #Inspiration #SelfGrowth #BreakBarriers #NeverGiveUp #Transformation #HeavyEquipmentOperator #WomenInMining

In this episode of the Generations of Wealth Podcast, host Derek Dombek sits down with 1031 Exchange expert Dave Foster to uncover powerful wealth-building strategies that allow real estate investors to defer taxes and maximize profits legally.

Dave shares creative strategies, real-life case studies, and insider tips to help investors grow their real estate portfolio while keeping more money in their pockets. Whether you're new to real estate or a seasoned investor, this episode is packed with game-changing insights!

🔹 Learn how to legally avoid capital gains tax 🔹 Discover the secrets of tax-free wealth creation 🔹 How to use 1031 Exchanges to scale your real estate empire

🔔 Like, Subscribe & Hit the Bell for More Wealth-Building Strategies!

🎯 Why You Should Listen

✔ Legally defer taxes & build generational wealth ✔ Learn creative loopholes to maximize your real estate investments ✔ Avoid common mistakes that can cost you thousands ✔ Insider strategies used by top investors to scale their portfolios

⏳ Time Stamps

00:00 - Welcome & Introduction 01:30 - Meet Dave Foster & His Journey into 1031 Exchanges 05:15 - What is a 1031 Exchange? (Explained Simply) 09:45 - How Dave Used 1031 Exchanges to Buy a Sailboat & Live Tax-Free 14:30 - The 1031 Exchange Step-by-Step Process 21:00 - The Biggest Misconceptions About 1031 Exchanges 26:45 - Creative 1031 Strategies That Most Investors Don't Know 32:20 - The Future of 1031 Exchanges & Real Estate Market Predictions 38:15 - How to Get Started & Avoid Costly Mistakes 40:00 - Final Thoughts & How to Connect with Dave

📌 Topics Covered

✔ What is a 1031 Exchange? ✔ How to legally defer taxes on real estate sales ✔ Creative strategies for using 1031 Exchanges ✔ The biggest mistakes investors make ✔ How to convert investment properties into personal residences ✔ How to structure deals to maximize returns ✔ What the future holds for real estate and tax laws

#RealEstateInvesting #1031Exchange #WealthBuilding #TaxFreeWealth #PassiveIncome #GenerationalWealth #RealEstateTaxStrategy #InvestmentHacks #FinancialFreedom #DaveFoster #DerekDombek #GenerationsOfWealth

🚨 The Truth About Reverse Mortgages – What They Don't Tell You! 🏡💰

Summary:

In this episode of The Generations of Wealth Show, host Derek Dombeck sits down with Laura Phillips, a 30-year mortgage industry veteran specializing in reverse mortgages. They dive deep into the myths, benefits, and potential pitfalls of reverse mortgages, breaking down how they work, who they’re for, and why they may (or may not) be a good financial tool. Whether you're a homeowner, real estate investor, or planning for retirement, this is a must-watch conversation that could change how you view home equity forever!

Key Takeaways:

✅ What is a Reverse Mortgage? (And how it’s NOT what you think!) ✅ Myth-Busting: Does the bank take your home? ✅ Who Should Consider a Reverse Mortgage? (And who should avoid it?) ✅ How to Use Reverse Mortgages to Build Wealth & Fund Retirement ✅ The Role of Reverse Mortgages in Estate Planning ✅ Common Mistakes & How to Avoid Foreclosure Risks

Time Stamps:

⏳ 00:00 – Welcome & Introduction ⏳ 02:15 – Who is Laura Phillips? ⏳ 05:30 – What Exactly is a Reverse Mortgage? ⏳ 08:45 – Biggest Myths About Reverse Mortgages ⏳ 13:20 – How to Qualify & Who Can Benefit ⏳ 18:50 – Real-Life Examples of Reverse Mortgages in Action ⏳ 25:10 – What Happens to Your Home & Heirs After You Pass Away? ⏳ 30:45 – How to Avoid Reverse Mortgage Pitfalls ⏳ 38:00 – Using Reverse Mortgages for Retirement & Wealth Strategy

Why Should You Listen?

🔹 Reverse mortgages are misunderstood! Learn the facts and separate truth from fiction. 🔹 Find out if this financial tool is right for you or your loved ones. 🔹 Discover how smart investors and retirees use reverse mortgages to their advantage. 🔹 Get expert insights from a 30-year industry veteran! 🔹 Avoid common mistakes that could cost you thousands!

#ReverseMortgage #ReverseMortgage #WealthBuilding #HomeEquity #Investing #RetirementPlanning #MortgageMyths #FinancialFreedom #EstatePlanning #GenerationsOfWealth

 

📢 Episode Summary:

In this episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with real estate expert BJ Gremillion, who shares his incredible journey from buying thousands of homes at foreclosure auctions to developing land and building a thriving turnkey investment business. BJ reveals how he navigated market downturns, overcame financing challenges, and built a recession-proof real estate portfolio. He also dives into creative financing, avoiding common investor mistakes, and the power of networking through masterminds. Whether you're a new or seasoned investor, this episode is packed with strategies for building wealth through real estate investing.

💡 Key Takeaways:

✅ From Foreclosures to Turnkey Success – BJ shares his journey through different phases of real estate investing. ✅ Adapting to Market Shifts – Lessons from experiencing downturns and how to pivot effectively. ✅ The Power of Turnkey Investing – How to generate passive income by letting a team handle acquisitions, renovations, and management. ✅ Creative Financing Strategies – Seller financing, private money lending, and structuring deals for cash flow. ✅ Avoiding Shiny Object Syndrome – Why focusing on one strategy leads to long-term success. ✅ Masterminds & Networking – How joining a mastermind can 10x your business and real estate knowledge. ✅ Building a Business That Runs Without You – BJ's insights on financial freedom and balancing work with family life.

🎧 Why Should You Listen?

✔️ Learn real estate strategies from someone who has closed thousands of deals. ✔️ Discover how to create passive income with turnkey rental properties. ✔️ Find out how to finance deals creatively without relying on banks. ✔️ Gain insights into avoiding common mistakes and pitfalls in investing. ✔️ Learn why networking and masterminds can transform your business. ✔️ If you’re interested in real estate, financial freedom, or passive income, this episode is a must-listen!

#RealEstateInvesting #TurnkeyRealEstate #PassiveIncome #WealthBuilding #CreativeFinancing #CashFlow #ForeclosureInvesting #RentalProperties #InvestmentProperties #FinancialFreedom #Entrepreneurship #MastermindGroup #RealEstatePodcast #BusinessGrowth #SellerFinancing #RealEstateSuccess #MarketTrends