Investing for Generational Wealth

Hosted by Keshav Kolur

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Episodes

Latest episode

May 2026

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EN-US

About the show

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.

Listen to episodes

60 recent

May 21, 202651 min

EP. 81 - Strategic Legal Planning For Sustainable Small Business Growth

In this episode, running a small business is one of the most rewarding investments you can make, but without the right legal foundation, even the most promising ventures can face costly setbacks. Matthew breaks down the essential legal planning every business owner needs and tackles the real challenges facing small businesses today.With over two decades of experience in business law, Matthew will discuss:- Legal strategies for growing and sustaining long-term business value- Issues facing small businessesMatthew Fornaro is a Florida-based business law attorney with over two decades of experience guiding entrepreneurs and families through every stage of their business journey. A mentor for new entrepreneurs and a trusted advocate for small and medium-sized businesses and have been recognized by Forbes.Join Matthew and Clive Capital for an insightful and empowering conversation that bridges the gap between smart legal planning and sound business investment.This is your opportunity to gain expert legal knowledge directly applicable to your business and investment goals, all in one focused session designed with the small business owner and investor in mind.

May 21, 202652 min

EP. 80 - Tax-Smart Wealth Building (Harvesting, Asset Location, Charitable Strategies)

Chad Taylor breaks down the real-world financial decisions high earners and newly liquid families face as their wealth grows. Drawing on over 20 years of experience in major brokerage firms including his role as SVP of Wealth Management at UBS, Chad shares practical, planning-driven strategies designed to optimize taxes, avoid costly mistakes, and build long-term financial clarity. Now leading Seapoint Wealth Advisors, he brings a more personalized approach to wealth management cutting through unnecessary complexity and focusing on what truly moves the needle.Join Chad Taylor and Clive Capital for a focused deep dive into tax-efficient strategies, smarter capital deployment, and disciplined wealth building without the overengineered noise.If you are navigating growing wealth and want to make smarter, tax-efficient decisions without overcomplicating the process, this is a conversation you won’t want to miss.

May 21, 202654 min

EP. 79 - The Wealth Strategies Hidden in Plain Sight

In this episode, Alan Porter dives into the financial strategies the wealthy use strategies most people never learn to help you legally eliminate or drastically reduce taxes in retirement.With decades of experience as a Certified Tax and Business Advisor, Alan will discuss:- How to create a tax-free retirement plan tailored to your goals.- Proven strategies to legally reduce or eliminate taxes on your investments and income.-The insider wealth-building tactics the wealthy rely on that most people never hear about.-How to protect your family and legacy while maximizing financial growth.Alan leads a powerhouse team of CPAs, tax attorneys, and elite financial professionals dedicated to delivering tax-free retirement solutions and bulletproof financial strategies. Featured in over 1,100 publications and bestselling author of Tax Free Retirement Solution, Alan has spoken at Harvard, West Point, and appeared on major media outlets including ESPN, Fox, ABC, and CBS.Join Alan and Clive Capital to gain insider insights and actionable strategies for building a tax-efficient, prosperous retirement.Don’t miss this opportunity to learn from one of the most trusted authorities in tax-free wealth planning. Take the steps today to secure your financial future.

May 21, 202648 min

EP. 77 - Inside the Minds of $10M Fund Managers

Join us for an insightful session that explores how fund managers identify, analyze and select investment opportunities in today’s dynamic financial markets.We will take a closer look at the decision-making process behind portfolio construction from evaluating potential investments to managing risk and maximizing returns. Participants will gain practical insights into the analytical frameworks, key metrics, and strategic thinking that fund managers use when determining which opportunities make it into their portfolios.Whether you are a student interested in finance, an aspiring investment professional, or simply curious about how investment decisions are made at the fund management level, this session will provide valuable perspectives on how successful investment strategies are developed.What you’ll learn:• How fund managers screen and evaluate investment opportunities• Key factors considered when selecting investments• The role of research, analysis, and risk management• Real-world insights into portfolio decision-makingDon’t miss this opportunity to step inside the mind of fund managers and better understand how investment decisions shape portfolios and markets.

April 17, 202636 min

EP. 78 - $10M Raised & What's Next: Clive Capital Q1 2026 Update

In this episode, the key macroeconomic trends driving today's investment landscape from sticky inflation and slowing GDP growth to tariff impacts, the AI Supercycle, and the real estate sectors best positioned to thrive. Transparent, asset-by-asset performance updates across our active portfolio of 1,100+ apartments, 16 industrial warehouses, and 47 oil and gas wells and share what's driving results across every investment class. Clive Capital identifies institutional-quality opportunities, evaluates risk and returns, and builds a diversified, cash-flowing portfolio outside of the stock market. This session delivers real, actionable perspective:-How macroeconomic shifts and AI are reshaping investment opportunities in 2026 -Transparent performance updates across Multifamily, NNN Industrial, Oil & Gas, and Private Debt -Key metrics Clive Capital uses to evaluate risk, cash flow, and equity growth -Upcoming opportunities including Iron Horse Energy Fund II, targeting 18–20% IRR Connect with Clive Capital: clivecapital.comDISCLAIMER: 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

March 4, 202651 min

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

Most families think avoiding money conversations keeps the peace. Jeffrey Condren says it's actually what tears them apart.In this episode, Jeffrey Condren, CFP® and Senior Vice President & Wealth Advisor at Mesirow 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 wealthThe 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 rightJeff'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 Jeffrey and his team at mesirow.comThis 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.

March 4, 202644 min

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 heldHow self-directed IRAs and solo 401(k)s workThe barbell strategy for tax-smart investingWhy six deals at $50K beats one deal at $375KWhat UBIT actually means for your returnsHow 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: @FitFinanceHenryLearn 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

February 10, 202649 min

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.comConnect with Clive Capital: clivecapital.comDISCLAIMER: 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

February 1, 202654 min

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

January 30, 202651 min

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