136 | Why 90% of Family Wealth Is Gone By the Third Generation (And How to Stop It) with DJ Van Keuren

136 | Why 90% of Family Wealth Is Gone By the Third Generation (And How to Stop It) with DJ Van Keuren

What separates the entrepreneurs who build lasting, generational wealth from those who watch it disappear by the second or third generation? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with DJ Van Keuren – Harvard educated family office real estate expert, founder of the Family Office Real Estate Institute, and a man who has personally managed real estate portfolios for some of the most prominent families in the country, including the Marriott family, to unpack the strategies, systems, and mindset shifts that turn entrepreneurial success into a lasting legacy. DJ brings decades of real-world experience navigating everything from luxury hotel acquisitions in New York City to distressed multifamily opportunities, and he doesn't hold back on exactly where wealthy families go wrong and what to do instead. Patrick and DJ dive deep into the four pillars of real estate wealth building - appreciation, depreciation, amortization, and cash flow and why the average family office allocates roughly 24% of its portfolio to real estate. DJ reveals the single biggest mistake business owners make once they accumulate significant wealth (hint: it's the same thing that made them successful in business, and they stop doing it), how to properly stress test a deal before you commit, why underwriting the operator matters far more than underwriting the deal itself, and why right now may be one of the most compelling buying opportunities in the 18.6-year real estate cycle. Whether you're evaluating your first syndication or building a multi-generational real estate portfolio, this conversation gives you the framework, the questions to ask, and the perspective to invest with confidence. Key Takeaways: * The average family office allocates ~24% of its portfolio to real estate, for good reason. Appreciation, depreciation, amortization, cash flow, and leverage all work together to build wealth in ways other asset classes simply can't match * The #1 mistake wealthy business owners make is applying zero structure to managing their own wealth, the same rigor (goals, strategy, quarterly reviews) that built the business needs to be applied to the portfolio * An Investment Policy Statement (IPS) is the foundation, it defines what you'll buy, what returns you're targeting, and whether future generations are part of the picture * Always underwrite the operator before the deal, a great property with a bad operator is a bad investment. Ask how they navigated the Great Recession, not just what returns they posted * Stress test every deal, model the worst case scenario (higher cap rate at exit, higher refinancing rates) and ask if you can live with that outcome before you commit * Real estate runs on an 18.6-year cycle, DJ believes we are currently at a prime buying point, with distressed multifamily assets hitting the market due to financial pressure, not property failure * Multifamily has historically never exceeded 11.6% vacancy - the resilience compared to commercial or office makes it a core holding for cash flow and downside protection * 70% of family wealth is lost by the second generation; 90% by the third - governance, family councils, and intentional planning are the antidote * Real estate's illiquidity is a feature, not a bug, it protects families from emotional decision-making and forces the long hold that builds real wealth * The optimal number of properties in a family real estate portfolio is 15, per FORE Institute research, funds can be an efficient path to that diversification without the management burden Learn More About DJ: * Family Office Real Estate Institute: fore.institute [https://fore.institute/] * DJ Van Keuren's personal website: djvankeuren.com [djvankeuren.com] Resources:    * Visit vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      * Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/] * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

135 | The Portfolio Income Mistake That's Silently Draining Your Wealth with Russ Gaiser & Mike Hoeflich

Are you leaving hundreds of thousands of dollars on the table with your retirement income strategy? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Russ Gaiser III and Mike Hoeflich - co-authors of the #1 bestselling book Beyond Breakeven: The Essential Guide to Social Security Optimization and founders of Retirement Income HQ of America, to tackle one of the most misunderstood challenges facing entrepreneurs today: turning a lifetime of accumulated wealth into a reliable, tax-efficient retirement income stream. Russ and Mike have helped thousands of couples stop guessing with their benefits and start building math-backed income plans, and in this conversation they pull back the curtain on the strategies most financial advisors either don't know or won't tell you. Patrick and his guests walk through the five pillars of retirement income optimization, expose the hidden conflict of interest that causes most advisors to give subpar Social Security advice, and break down exactly how high-net-worth entrepreneurs can design a retirement where they potentially owe zero in federal taxes. From the dangers of dollar cost ravaging and sequence of returns risk, to the tax time bomb hiding inside most 401k accounts, to the overlooked trap that leaves surviving spouses financially vulnerable, this episode is packed with actionable, math-backed strategies that can permanently change your retirement outcome. Whether you're five years from retirement or already in it, this is a conversation you can't afford to miss. Key Takeaways: * Claiming Social Security at age 70 versus age 62 can mean at minimum 77% more monthly income for life * Most financial advisors have a built-in conflict of interest when advising on Social Security timing * Dollar cost ravaging, not dollar cost averaging, is the real risk retirees face when drawing from market-dependent portfolios * A large traditional 401k or IRA can become a tax time bomb at RMD age, forcing taxable withdrawals that spike your tax bracket and Medicare premiums * Up to $600–$700 per month in extra Medicare premiums (IRMAA) can be triggered by poor income planning * At least 15% of Social Security income is always tax-free, making it one of the most tax-efficient income sources available * The surviving spouse tax trap is one of the most overlooked risks in retirement planning * A successful retirement income plan starts with knowing exactly how much you need and just as importantly, how much you don't Learn More About Mike and Russ: * 📘 beyondbreakevenbook.com [https://beyondbreakevenbook.com/] Episode Resources: * The Intelligent Investor by Benjamin Graham [https://www.amazon.com/Intelligent-Investor-Third-Investing-Financial/dp/0063497476/ref=sr_1_1?adgrpid=1334807683360996&dib=eyJ2IjoiMSJ9.KlxwzEYN6nItyVP_hxVDHL8eAZ0t52Haq8bXV9AGyrduUM3WUj2BvcfCd3XO8kB2rCuzFTNTGpdiLCOZIOSI6H6NA9T50difLaEJesfRdI4QylmE0HC6dtETqPf-9M7WqguT1lHWEm6epcdjtZQqwTGVvHKD8V39zQMpLPGNCDsr_oftAmBlzHoZslfrFj8qN2zg4pBUUwWypkaPVGbbqlU6nY2C6tjuEqp7fiLAevg.hNdd9G5t5f_AMrI9K-K_eFmRP3oDG8UimxTwztN6CtE&dib_tag=se&hvadid=83425719894235&hvbmt=be&hvdev=c&hvlocphy=93688&hvnetw=o&hvqmt=e&hvtargid=kwd-83425832544692%3Aloc-190&hydadcr=21965_13325435&keywords=the+intelligent+investor+by+benjamin+graham&mcid=0c511cc5d0f1302c846c7b812858f07e&msclkid=61bfde3540d019ebd34ab42bbc8c9ebe&qid=1780415585&sr=8-1] Resources:    * Visit vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      * Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/] * Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies] * Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast] * Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/] Credits:     * Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/] * Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e] * Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] * Audio, video, research and copywriting by Victoria O'Brien

134 | The IRS Loopholes Keeping Millions in Entrepreneur Pockets with Michael Moffa

What if the tax strategy your CPA has never mentioned could legally eliminate hundreds of thousands of dollars in tax liability and generate cash flow at the same time? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with returning guest Michael Moffa, founder of Prosperity Tax Advisors, for a masterclass in advanced tax strategy built specifically for high-income entrepreneurs. Michael brings nearly 25 years of experience in private wealth advising and leads the only tax advisory firm in the country housing eight professional credentials under one roof, giving business owners access to elite-level tax planning, wealth management, and exit strategy guidance that most CPAs simply cannot provide. Patrick and Michael pull back the curtain on the IRS-compliant tax strategies that top earners are quietly executing right now, from cost segregation and bonus depreciation in real estate, to a healthcare technology investment strategy that turns a $100,000 investment into a $700,000 tax deduction with 7-to-1 leverage. Listeners will gain a clear understanding of what separates a legitimate tax strategy from a costly mistake, including how economic substance, material participation, and proper documentation can make a strategy both powerful and audit-proof. Whether you are a business owner frustrated by a growing tax bill, planning a future liquidity event, or simply ready to stop leaving money on the table, this episode delivers the advanced tax planning insights that could change the trajectory of your wealth. Key Takeaways: * Most entrepreneurs are stuck in reactive, compliance-based tax planning - a proactive strategy can save hundreds of thousands annually * A legitimate tax deduction must meet three criteria: ordinary, necessary, and reasonable in amount under IRC §162A * The economic substance doctrine requires that a transaction change your financial position beyond tax savings alone * A $100,000 investment in a healthcare technology strategy can generate a $700,000 deduction and $210,000 in tax savings at a 30% tax rate, compared to $24,000 in savings through a traditional oil and gas investment * Captive insurance (831(b) plans) can be a powerful strategy when properly structured but policies must be ordinary and necessary to your specific business * Wyoming LLCs offer privacy protections and charging order protection (COPE), making them ideal for holding passive assets outside your operating business * Tax strategies should live on the personal side, not inside the business, to protect EBITDA and maximize your business sale multiple * Documentation, third-party valuations, and audit defense are non-negotiable components of any advanced tax strategy * Crypto gains can be offset through strategies beyond a Charitable Remainder Trust, without locking up your capital Learn More About Michael: * Prosperity Tax Advisors – https://prosperityta.com [https://prosperityta.com] * Michael Moffa – mmoffa@prosperityta.com [mmoffa@prosperityta.com] Resources:    Visit www.vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/]   Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies]       Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast]      Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/]      Credits:     Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/]     Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e]     Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] Audio, video, research and copywriting by Victoria O'Brien

133 | The Investment Game Is Rigged… Here's How to Get On the Right Side of It with Mike Collins

What if the most powerful wealth-building investment on the planet has been deliberately kept out of reach, until now? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Mike Collins, founder of Alumni Ventures, one of the most active venture capital firms in the United States, for a conversation that will fundamentally change the way entrepreneurs think about building and growing wealth. Mike brings over three decades of venture capital experience, starting at TA Associates in Boston in 1986, and has spent the last 12 years cracking open access to elite startup deals for everyday investors, the same deals backed by Andreessen Horowitz, Sequoia, and Benchmark and making them available to a community of 25,000 individual investors through Alumni Ventures. Patrick and Mike go deep on exactly how venture capital works, how it differs from private equity, and why a diversified portfolio of startups may actually be one of the most prudent moves an entrepreneur can make with their wealth. They unpack the explosive opportunities emerging right now in AI, defense tech, nuclear energy, and biotech drug discovery, and reveal why 2026 is shaping up to be one of the most target-rich environments for venture investing in a generation. Mike also shares the Alumni Ventures framework for evaluating deals, the tax advantages savvy investors are using, including QSBS, Roth IRA conversion strategies, and cash balance plan rollovers and why the illiquidity of venture capital is actually one of its greatest strengths for long-term wealth building. This is a must-listen for any entrepreneur serious about putting their money where the real value is being created. Key Takeaways * The best venture capital deals have historically been locked behind institutional access; Alumni Ventures pools capital from 25,000 individuals to co-invest alongside tier-one VCs like Andreessen Horowitz, Sequoia, and Benchmark under the same terms * A smart VC strategy targets a portfolio of approximately 100 companies built over 3–4 years - 5–10% of those investments can generate returns large enough to make the entire portfolio worthwhile * Venture capital and private equity are fundamentally different, VC bets on early-stage growth companies while PE focuses on established businesses, leverage, and financial engineering * Adding alternatives like venture capital to a portfolio reduces overall volatility and protects against the compounding damage that market drawdowns cause to long-term wealth * The illiquidity of venture capital is a feature, not a flaw, it eliminates emotional short-term decision making and forces the patient, disciplined approach that actually builds generational wealth * AI is just one of several exciting frontiers right now, nuclear energy, space communications, defense tech, and AI-driven drug discovery are all generating compelling venture opportunities in 2026 * Powerful tax strategies including QSBS (Section 1202), Roth IRA conversions on discounted private holdings, and cash balance plan rollovers can dramatically reduce or eliminate the tax burden on venture capital gains * Alumni Ventures offers flexible entry points including diversified funds, sector-specific funds, and individual deal access so investors can participate at whatever level fits their goals and risk tolerance * By the time a company goes public, the most explosive growth phase is already over; getting in early through venture capital means investing where value is actually being created, not chasing it after the fact Learn More About Mike: * Website: av.vc [https://av.vc] Resources:    Visit www.vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/]   Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies]       Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast]      Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/]      Credits:     Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/]     Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e]     Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] Audio, video, research and copywriting by Victoria O'Brien

132 | More Americans Drink Coffee Than Water - Here's Why That's an Investment Opportunity with Adam Jason

Did you know more Americans drink coffee every day than a glass of water and yet almost nobody thinks of coffee as an investment opportunity? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Adam Jason, co-founder of Green Coffee Company and former Wall Street capital markets attorney, to unpack one of the most compelling alternative investment opportunities available to accredited investors today. Patrick and Adam explore how Green Coffee Company became the largest coffee producer in Colombia, why the traditional coffee supply chain is fundamentally broken, and how their farm-to-cup model is disrupting an industry worth billions. From major retail partnerships with Target and Walgreens to serving as the official coffee for Carnival Cruise Lines and the Western US National Parks, Green Coffee Company is quietly building something extraordinary and a Nasdaq IPO is on the horizon within 18 months. For entrepreneurs and high-net-worth investors looking to diversify beyond stocks and bonds, this episode of the Vital Wealth Strategies Podcast is essential listening. Patrick and Adam break down why alternative investments like coffee commodities can dampen portfolio volatility, how pre-IPO opportunities create asymmetric upside, and why traceability and sustainability aren't just feel-good buzzwords, they're competitive advantages driving real revenue growth. Whether you're a seasoned investor exploring private market opportunities or an entrepreneur looking to align your wealth-building strategy with your values, this conversation delivers the insight, inspiration, and actionable perspective you need to think differently about where your money works hardest. Key Takeaways: * Coffee is the second most traded commodity on earth behind petroleum, with 2 billion cups consumed daily worldwide * Green Coffee Company owns approximately 10,000 acres and 10 million coffee trees, making them the largest coffee producer in Colombia * Their farm-to-cup supply chain model provides full traceability, a major differentiator as ESG standards and ethical sourcing demands increase * The Juan Valdez brand has grown from zero to 2,500+ retail doors in just over a year, including Walgreens (1,400 stores) and Target (317 stores) * Alternative investments like coffee can reduce portfolio volatility by operating independently of traditional stock and real estate markets * Green Coffee Company is structured as a US Delaware holding company, giving investors the comfort of US law, US banking, and a familiar legal framework * A Nasdaq IPO is targeted within 18 months, creating a potential pre-IPO opportunity for accredited investors with a $100,000 minimum commitment * To connect with Adam Jason and learn more about investment opportunities, find him directly on LinkedIn Learn More About Adam: * Adam Jason's LinkedIn profile: Adam Jason | LinkedIn [https://www.linkedin.com/in/adam-jason-98a22612/] Resources:    Visit www.vitalstrategies.com [http://www.vitalstrategies.com/] to download FREE resources      Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs [https://www.vitalwealth.com/podcasts/]   Follow on Instagram at https://www.instagram.com/vital.strategies [https://www.instagram.com/vital.strategies]       Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast [https://www.facebook.com/VitalStrategiesPodcast]      Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ [https://www.linkedin.com/in/patricklonergan/]      Credits:     Sponsored by https://www.vitalwealth.com/Vital Wealth [https://www.vitalwealth.com/]     Music by https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480eCephas [https://open.spotify.com/artist/6ullBRZTTK0lT7fUqbgbKD?si=GlsDiJdeSg2bLkb3lxO0Ig&fbclid=IwAR1Gn1Jz2thWofOrFilg6HV1AcxV5AumMjNyTH_5xvrtQsnVuPElY9XzVFU&nd=1&dlsi=fed5b9538f23480e]     Art work by Two Tone Creative  [https://www.twotonecreative.com/strategy-consulting/] Audio, video, research and copywriting by Victoria O'Brien