Investing for Generational Wealth

Keshav Kolur
  • 5.0 (5)
  • INVESTING
  • UPDATED WEEKLY

Are you looking to grow your wealth passively while minimizing your risk? Whether you are interested in real estate, small business, private lending, venture capital, or other time-tested wealth-building strategies, you’re in the right place. Every week, we invite domain experts to speak on investments, tax and legal strategies, and much more, all with the goal of helping you build your portfolio wealth. Like and subscribe now so you don't miss an episode.

  1. MAR 4

    EP. 76 - The Case for More Conflict, Not Less, When Talking About Wealth with Jeff Condren

    Most families think avoiding money conversations keeps the peace. Jeff Conran says it's actually what tears them apart. In this episode, Jeff Conran, CEFP and Senior Vice President & Wealth Advisor at Maslow Wealth Management, breaks down why the families that fight smarter about money are the ones that keep it across generations. With 20 years of experience advising families through market cycles, business transitions, and the messy stuff nobody wants to talk about at the dinner table, Jeff has seen firsthand what happens when wealth conversations get swept under the rug. Spoiler: it never ends well. We cover: Why "healthy conflict" isn't an oxymoron when it comes to family wealth The real reason founders are terrified to hand over the business (and why their kids feel like they'll never be trusted) -Fair vs. equal: the hardest conversation parents will ever have with their kids -How to talk to your children about money at every age, yes, even with a $20 bill and a stuffed animal -Trust structures, governance, and when winging it as a family stops working -The financial literacy gaps hiding in plain sight in affluent households -When a wealth advisor knows it's time to step aside and bring in a therapist -Tax strategies that quietly create family tension nobody saw coming -What it actually looks like when a generational transition goes right Jeff's core message is simple: clarity prevents conflict. The families who normalize tough conversations early don't just preserve wealth. They strengthen it. 🔗 Learn more about Jeff and his team at nesiro.com This is Investing for Generational Wealth, presented by Clive Capital. We help high-earning professionals invest outside the stock market through alternative investments like real estate, oil & gas, private credit, and more. Disclaimer: We are not financial advisors. All investments carry risk. Please consult your CPA and attorney before making any investment decisions. Don't forget to like, subscribe, and hit the notification bell so you never miss an episode.

    51 min

  2. MAR 4

    EP. 75- Diversifying into Private Equity using Retirement Monies with Henry Yoshida

    🚀 Your 401(k) can do way more than stocks and mutual funds. Henry Yoshida, CEO of Rocket Dollar, former Merrill Lynch veteran, and founder of Honest Dollar (acquired by Goldman Sachs), reveals how to unlock your retirement accounts for private investments like real estate, oil & gas, and more. In this episode: Why 83% of $100M+ revenue companies are privately held How self-directed IRAs and solo 401(k)s work The barbell strategy for tax-smart investing Why six deals at $50K beats one deal at $375K What UBIT actually means for your returns How to plan early retirement drawdowns before 59½ 💡 Bottom line: stop chasing stock picks. Focus on what you can control. Connect with Henry: https://www.rocketdollar.com Instagram: @FitFinanceHenry Learn more about Clive Capital: https://www.clivecapital.com ⚠️ Not financial advice. All investments carry risk. Consult your CPA and attorney before investing #SelfDirectedIRA #PrivateInvesting #AlternativeInvestments #RetirementPlanning #401k #RocketDollar #CliveCapital #GenerationalWealth #PassiveIncome

    44 min

  3. FEB 10

    EP. 74 - The Tax Playbook for Entrepreneurs Building Generational Wealth with Mike Milligan

    Your CPA files what happened. They don't plan what could happen. And that difference is costing you wealth. In this episode, Mike Milligan, CFP® and founder of One Oak Financial, breaks down 6 tax strategies every entrepreneur should be using right now. Mike doesn't just teach this stuff, he lives it. He moved his family to Puerto Rico and dropped his effective tax rate from 37% to 4%. His 28 year old son has a million dollar Roth IRA. His 24 year old has $600K. All tax free. All from strategies he used in his own business. We cover S-Corp structuring, the Augusta Rule, accelerated depreciation, family payroll, solo 401(k)s, and geographic arbitrage. If you're a high earner still overpaying in taxes, this episode is your wake up call. Connect with Mike Milligan: mikemilligan.com Connect with Clive Capital: clivecapital.com DISCLAIMER: This episode is for educational purposes only. We are not financial advisors. All investments are subject to risk including the possible loss of principal. Please consult your CPA and attorney before making any financial decisions. #TaxStrategy #Entrepreneurship #WealthBuilding

    49 min

  4. FEB 1

    EP. 73 - 401(k) Optimization — Maximizing Tax Deductions & Employee Benefits with Paul Sippil

    Are you unknowingly losing thousands in hidden 401k fees? Forensic 401k consultant Paul Sippel exposes how businesses are being charged excessive fees that come directly out of employee accounts, without ever receiving an invoice. You'll hear shocking stories, including one company that unknowingly paid a dead advisor for nearly a decade. Paul breaks down how to investigate your plan's fees, negotiate with providers, and structure your 401k to maximize tax deductions while eliminating unnecessary costs. Whether you're a startup founder or running an established firm, this episode will change how you think about retirement benefits. Learn more at paulsippil.com. Reach Paul: Website: https://www.paulsippil.com/ Youtube: @paulsippil #401k #RetirementPlanning #TaxDeductions #HiddenFees #EmployeeBenefits #WealthBuilding

    54 min

  5. JAN 30

    EP. 72 - Hidden Fees and Precautions for Syndication Investors with Richard Crouch

    Ever wondered what hidden fees and legal traps could be quietly eroding your returns in real estate syndications? In this episode, we sit down with Richard Crouch, a commercial real estate attorney with over two decades of experience and chair of the business group at Woods Rogers, to uncover what most investors overlook before wiring their money. Richard breaks down the critical clauses you need to scrutinize in operating agreements and PPMs, from waterfall distributions and fee disclosures to manager removal provisions and exit strategies. He shares real examples of investors being "held captive" in underperforming deals and explains why the absence of certain protective language should be a major red flag. Whether you're evaluating your first syndication or your tenth, this conversation will sharpen your due diligence process and help you ask the right questions before committing capital. Learn what separates reputable sponsors from the rest and how to protect yourself when deals don't go as planned. Contact Richard Crouch: 📧 richard.crouch@woodsrogers.com 📞 757-446-8684 🌐 www.woodsrogers.com

    51 min

  6. JAN 2

    EP. 71 - Why Mobile Home Park Investing Is Recession-Proof | Jack Martin (52TEN)

    Is mobile home park investing really recession-proof? In this webinar, Jack Martin, co-founder of 52TEN, breaks down why mobile home parks are considered one of the most resilient real estate asset classes—especially during economic uncertainty. With experience across $450M+ in real estate transactions, 1,600 lots across 4 states, and $55M+ in private investor capital, Jack shares the real-world strategies that help investors generate steady income across market cycles. What You’ll Learn: - Why mobile home parks are widely viewed as recession-resistant - How this asset class produces consistent cash flow in any market - Key risk-mitigation strategies used by professional operators What makes mobile home parks different from other real estate investments About Jack Martin: Jack Martin is the co-founder of 52TEN and an experienced real estate operator with a disciplined, investor-first approach. He has helped 200+ investors achieve predictable income and long-term stability through mobile home park investing. If you’re looking to add a recession-resilient real estate strategy to your portfolio, this webinar is a must-watch. Reach Jack: 52ten.com admin@52TEN.com Reach Clive Capital Website: https://www.clivecap.com/ LinkedIn: https://www.linkedin.com/in/keshavkolur/ Calendly: https://calendly.com/keshavkolur/30min Linkedin: https://www.linkedin.com/in/johnlai/ https://calendly.com/laijohn/30min Email: ir@clivecap.com Sms: +1 650-229-5450

    41 min

  7. JAN 2

    EP. 70 – Long-Term Care Planning: What to Consider & Avoid | Raymond Lavine

    Long-term care planning is one of the most overlooked—and most critical—parts of a sustainable financial plan. In this webinar, Raymond Lavine, founder of Lavine LTC Benefits, breaks down what families and investors need to know about planning for extended care, protecting assets, and avoiding common (and costly) mistakes. Drawing from both professional expertise and personal experience, Raymond shares practical insights to help you safeguard your health, wealth, and legacy. What You’ll Learn: - Why long-term care and caregiving benefits are essential to your financial plan - The hidden risks of delaying care planning—and how to avoid them - How long-term care insurance can protect your estate and loved ones - Common misconceptions that leave families financially exposed About Raymond Lavine: Raymond Lavine is a respected voice in financial and wealth planning, specializing in long-term care solutions. He is the founder of Lavine LTC Benefits, a U.S. Army veteran, and a co-author of Empathy and Understanding in Business with Chris Voss. Raymond has also appeared on national TV, including Moving America Forward. Whether you’re planning for yourself, your family, or your investors, this conversation offers valuable guidance for creating peace of mind across generations. Reach Raymond: https://www.lavineltcins.com/ LinkedIn: https://www.linkedin.com/in/ltc-benefits/ Reach Clive Capital Website: https://www.clivecap.com/ LinkedIn: https://www.linkedin.com/in/keshavkolur/ Calendly: https://calendly.com/keshavkolur/30min Linkedin: https://www.linkedin.com/in/johnlai/ https://calendly.com/laijohn/30min Email: ir@clivecap.com Sms: +1 650-229-5450

    38 min

  8. 12/11/2025

    EP. 69 - From Corporate to Freedom: Brian Herriot’s Blueprint for a Life You Control

    In this episode of Investing for Generational Wealth, host John Lai of Clive Capital sits down with Brian Herriot—author, speaker, and founder of Herriot Financial—to explore what meaningful freedom really looks like. Brian shares his personal journey from a traditional corporate management career to building a lifestyle centered around time freedom, purpose, and intentional living. He breaks down the difference between financial independence and true freedom, and how shifting your beliefs around money can reshape your life. What You’ll Learn in This Episode - The difference between time freedom and financial independence - How to transition from a corporate environment to a flexible lifestyle - Strategies Brian uses for investing and wealth-building - Why cash can be a powerful tool for lifestyle design - How to rethink financial beliefs to support your goals - A preview of Brian’s upcoming book and his mission to help others Whether you're a high achiever, entrepreneur, or someone seeking more control over your time, this conversation offers practical insights for designing a life that aligns with your values. Reach Brian: https://timefreedomcalculator.com/ Reach Clive Capital Website: https://www.clivecap.com/ LinkedIn: https://www.linkedin.com/in/keshavkolur/ Calendly: https://calendly.com/keshavkolur/30min Linkedin: https://www.linkedin.com/in/johnlai/ https://calendly.com/laijohn/30min Email: ir@clivecap.com Sms: +1 650-229-5450

    40 min
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About

Are you looking to grow your wealth passively while minimizing your risk? Whether you are interested in real estate, small business, private lending, venture capital, or other time-tested wealth-building strategies, you’re in the right place. Every week, we invite domain experts to speak on investments, tax and legal strategies, and much more, all with the goal of helping you build your portfolio wealth. Like and subscribe now so you don't miss an episode.

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