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. 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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 10/08/2025

    EP. 68 - Financial Independence & Retiring Early (FIRE)

    What does it really take to retire early—and not just scrape by, but thrive? In this candid and inspiring conversation, John Lai, Co-Principal of Clive Capital, shares how he recently retired from Amazon to pursue the FIRE lifestyle (Financial Independence, Retire Early). Joined by fellow Clive Capital Principal Keshav Kolur, the two dive deep into the mindset, math, and strategies that led John to early retirement—and how you can take steps toward your own financial independence. What You’ll Learn: ✅ The different flavors of FIRE (Lean, Fat, Barista, Coast, and more) ✅ How to calculate your own FI number (and know if you’re there) ✅ The real story of how John reached FIRE—beyond the 401(k) ✅ The decumulation phase: how to think about spending in retirement ✅ Tax strategies for both the accumulation and drawdown years About the Speakers:John Lai recently left a high-level role at Amazon to embrace full-time financial freedom. With a background in big tech and an eye for alternative investments, John brings a practical, thoughtful voice to the FIRE conversation. Keshav Kolur, Clive Capital’s CEO and an early investor in real estate and private equity, provides a complementary perspective on building wealth through passive income and strategic portfolio planning. 📌 Whether you’re early on your FIRE journey or already halfway there, this episode will give you the insights, inspiration, and tactical ideas you need to move forward with confidence. 🔔 Subscribe for more real-world FIRE stories, passive investing strategies, and wealth-building insights: Reach Clive Capital Website: https://www.clivecap.com/ LinkedIn: https://www.linkedin.com/in/keshavkolur/ Linkedin: https://www.linkedin.com/in/johnlai/ Calendly: https://calendly.com/keshavkolur/30min https://calendly.com/laijohn/30min Email: keshav@clivecap.com Sms: +1 650-229-5450

    44 min

  8. 10/03/2025

    EP. 67 - Stop Overpaying Taxes: Invest in Oil & Gas Projects

    Oil & Gas Investing Webinar Discover how oil and gas investing can diversify your portfolio, create passive income, and unlock powerful tax advantages.In this exclusive educational webinar, we’ll share strategies that helped our investors reduce over $1M in taxable income in just 9 months—while building steady cash flow from 16 wells. You’ll Learn: ✅ How oil & gas projects compare to other private equity investments✅ Unique tax incentives (up to ~$80K savings per $100K invested)✅ How to evaluate operators, projects, and risk/reward✅ Case studies and success stories✅ Insights into our upcoming $100M fund launch Whether you’re a seasoned investor or exploring alternatives for the first time, this webinar will equip you with knowledge to make smarter, tax-efficient decisions. 📌 Don’t miss this chance to learn how energy investing can strengthen your portfolio and maximize returns! Reach Clive Capital Website: clivecap.comLinkedIn (Keshav): /keshavkolurCalendly (Keshav): ScheduleLinkedIn (John): /johnlaiCalendly (John): ScheduleEmail: ir@clivecap.comSMS: +1 (650) 229-5450

    58 min
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5
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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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