Think Outside The Stocks

Hosted by Madhavi Jain

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Latest episode

Aug 2026

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EN-US

About the show

Most busy professionals, especially high-skilled, high-income earning first generation immigrants, tech professionals and doctors alike, are unaware of the ways of the ultra-wealthy in this country to grow, preserve, protect and pass the generational wealth. Think Outside the Stocks is a podcast focused on educating you to generate multiple streams of passive income, break out of wall street barrier, move towards financial freedom and a life of purpose and passion. Every week, your host Madhavi Jain, an immigrant from India and ex-IT professional from one of the top 5 consulting firms, will bring you industry experts to educate you on risk-managed passive investments in commercial real estate, an efficient savings strategy with Infinity Banking and discussion with experts in tax, legal, estate planning, life protection etc, a holistic point of view for you. Join us to learn and also to draw clues from the success stories of these experts, on how do they "Think Outside the Stocks", so you can too! Please note: This podcast is for educational and informational purposes and should not be considered professional advice.

Listen to episodes

52 recent

August 18, 202659 min

EP 49 - The "Holy Grail" Real Estate Strategy Most Passive Investors Miss | Featuring Glenn Hanson

How can passive real estate investors step up their strategy and participate on the General Partner (GP) side of the business? In this episode of Think Outside The Stocks, host Madhavi Jain sits down with serial entrepreneur, pilot, and real estate veteran Glenn Hanson (Colony Hills Capital). With over $1.3 billion in real estate transactions under his belt, Glenn shares how investors can move beyond traditional LP check-writing to build long-term, enterprise-level wealth through GP stakes. Glenn dives deep into the power of systemizing businesses for private equity exits, navigating market cycles, diversifying risk across entire portfolios, and why resilience is the ultimate asset for any investor or entrepreneur. What You'll Learn in This Episode: Understanding GP Stakes: How passive investors can invest in the operating business behind syndications for high-multiple exit opportunities. Building Scalable Systems: Lessons from scaling manufacturing, pet crematory roll-ups, and $1B+ in multifamily portfolios. Navigating Market Volatility: How rising interest rates impact real estate and where the biggest opportunities lie today. Wealth Protection & Mentorship: The importance of joining elite mastermind circles to preserve and pass down generational wealth. Giving Back: Glenn’s inspiring story of founding the Hansen Initiative for Language and Literacy (HILL) to support children with dyslexia. Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

June 23, 20261 hr 4 min

EP 48 - Why Smart Women Play Small With Money (with Liz Faircloth)

Why do so many successful, smart women hesitate when it comes to investing and building wealth? In this episode of Think Outside the Stocks, host Madhavi Jain sits down with real estate powerhouse Liz Faircloth. Liz is the co-founder of a 55,000+ member women's investing community that manages nearly $2 billion in collective assets. Together, they discuss how to break through financial fear, shift your mindset from saving to investing, and build generational wealth on your own terms. You’ll also learn the golden rules of real estate partnerships and how to define your financial "North Star." If you’re ready to step into your financial power and stop relying on the Wall Street roller coaster, this episode is for you! Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

October 31, 202559 min

EP 47: The #1 Retirement Killer That's NOT the Stock Market (Most People Miss This)

In this episode of Think Outside the Stocks, host Madhavi Jain welcomes Chris Orestis, President of Retirement Genius, to discuss a revolutionary approach to retirement planning. With over 25 years of experience, Chris shares valuable insights into how retirees can protect their wealth and prepare for the financial demands of long-term care. Chris breaks down the process of using life insurance settlements as a way to fund long-term care, a strategy that can help families avoid depleting their savings. The discussion covers the importance of planning ahead for healthcare costs, the role of life insurance in securing a dignified retirement, and how small decisions made today can impact your future financial well-being. Whether you're nearing retirement or still in your working years, this episode will provide you with the tools to safeguard your wealth, plan for long-term care, and protect your family's future. Timestamps: 0:00 - Importance of acting today for retirement and financial planning. 0:13 - Chris Orestis emphasizes the need for immediate action. 1:01 - Introduction of Madhavi Jane and the focus of the podcast. 1:26 - Madhavi introduces Chris Orestis as the “Retirement Genius.” 3:00 - Chris talks about using life settlements for long-term care. 4:03 - Chris shares his background and involvement in retirement planning. 5:02 - The benefits of life settlements for paying for care. 6:24 - Chris discusses his media presence and expertise. 7:02 - Chris explains his transition from politics to retirement planning. 10:34 - The growing need for long-term care solutions. 14:39 - How life settlements can help seniors pay for care. 18:04 - How life insurance policies qualify for life settlements. 21:50 - The steps involved in the life settlement process. 27:10 - Chris explains the process of closing a life settlement. 32:01 - Tax implications of life settlements and annuities. 35:58 - Combining life insurance, long-term care insurance, and annuities. 39:50 - Chris’s advice on securing life insurance and long-term care. 42:10 - Planning for retirement and healthcare in advance. 44:02 - Chris talks about estate planning and the importance of health. 47:01 - Chris emphasizes family and financial planning for retirement. 50:00 - Rapid-fire Q&A segment begins. 52:16 - Real-life story of how life settlements helped a family. 54:02 - Chris discusses Social Security and Medicare solvency issues. 57:01 - Closing thoughts on health and long-term care planning. 59:20 - Madhavi ends the episode and promotes the free guide. Links To Connect With Chris: Website: https://chrisorestisrg.com/ Email ID: chris@retirementgenius.com LinkedIn : https://www.linkedin.com/in/chrisorestis/ Links for Viewers to Connect Madhavi Jain: Website: https://thinkoutsidethestocks.com/ LinkedIn: / madhavinadejain Instagram: / thinkoutsidethestocks Podcast:https://podcasts.apple.com/us/podcast… Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

August 22, 202557 min

EP 46: Private Credit & Pilot Training: Investing Beyond Wall Street | Brandon Martini & Madhavi Jain

In this episode of Think Outside the Stocks , host Madhavi Jain sits down with Brandon Martini, co-founder and COO of Stratus Financial, to explore an alternative investment class that helps aspiring pilots finance their training while delivering strong, risk-adjusted returns for investors. Brandon shares his journey from Navy veteran and airline pilot to entrepreneur, building one of the fastest-growing companies in America. He explains how Stratus Financial bridges a critical funding gap for future aviators, discusses how private credit is becoming a powerful investment vehicle for accredited investors, and dives into risk management, repayment structures, and the long-term global demand for pilots. Beyond business, Brandon reflects on the importance of diversification — from real estate and Bitcoin to fine art and whiskey — and how he integrates meditation, scuba diving, and giving back through scholarships into his life philosophy. 🎧 What You’ll Learn from This Episode: How private credit works for aviation training – why financing pilot education can deliver both strong returns and real-world impact. Risk management strategies in private lending – from co-signers to structured repayments that protect investor capital. The power of diversification – how Brandon balances investments across gold, Bitcoin, fine art, real estate, and private businesses. Impact-driven investing – stories of students who became commercial airline pilots thanks to Stratus Financial’s model. Mindset lessons for growth & balance – from scuba diving as meditation to building daily habits for personal and financial success. This episode is a must-listen for accredited investors, entrepreneurs, and anyone interested in the intersection of impact and income. Link for Viewers: Think Outside the Stocks - https://thinkoutsidethestocks.com/ Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

August 8, 20251 hr 1 min

EP:45 Think Outside the Stocks: Unveiling the $230B Life Settlement Market with Matthew Paine (Part 2)

What if your life insurance policy could do more than just offer peace of mind—it could become a powerful wealth-building asset ? In Part 2 of this eye-opening series, Madhavi Jain continues her conversation with Matthew Paine , a seasoned expert in the life settlement market, to uncover one of the most overlooked yet powerful investment opportunities available today: life settlements . This episode dives deep into: ✅ How life settlements offer actuarially priced, non-correlated returns ✅ Why institutional investors have quietly invested billions in this space ✅ The ethical impact of helping seniors extract value from unwanted policies ✅ How investors can leverage these policies for stable, passive income ✅ The critical link between Infinite Banking and policy efficiency 💡 If you’ve ever heard the phrase “buy term and invest the rest,” this episode will challenge that thinking and show you a smarter, alternative path to grow and protect your wealth. 🔁 Missed Part 1? Catch it here for the full foundation on how life insurance can become an investment-grade asset. 📢 Share this episode with fellow investors who want to diversify their portfolio and think beyond conventional strategies. 👉 Subscribe to Think Outside the Stocks today to access more expert advice and strategies for building wealth through real estate investing! Link for Viewers: Think Outside the Stocks - https://thinkoutsidethestocks.com/ Matthew's Website- https://www.lifecap.com/ Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

August 1, 202554 min

EP 45: Banks, Billionaires, and Life Insurance: What They’re Not Telling You (Part 1)

🔍 Join host Madhavi Jain on Think Outside the Stocks as she sits down with Matthew Paine, Managing Director at LifeCap and a 24-year veteran who's revolutionizing how we think about life insurance as an investment vehicle. This conversation challenges the widespread "buy term and invest the difference" philosophy, revealing why it could be sabotaging your family's financial future. Learn how sophisticated investors, institutions, and ultra-wealthy families leverage life insurance beyond simple protection—transforming it into a strategic wealth accumulation tool with unmatched tax benefits. This episode is essential viewing for investors, parents, and finance professionals ready to expand their wealth-building toolkit. 🎯 Key Discussion Points: The hidden flaws in traditional "buy term" strategies Get know the life insurance's wealth-building potential Maximizing tax benefits and asset protection features Elite financial strategies used by banks and billionaires Practical applications of infinite banking and generational wealth transfer ⏭️ Don't miss Part 2, featuring specific implementation tactics and sophisticated structures you can put into practice immediately. Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

July 14, 202557 min

EP 44: Why EVERY Millionaire Has Trauma Around Money (Wealth Manager Exposes The Truth)

What if wealth management wasn’t just about numbers, but about transforming who you become? In this profound episode, host Madhavi Jain sits down with Tim “Jai” Baker, a wealth manager who has spent over four decades revolutionizing how we think about money, values, and life purpose. After losing his daughter in 2005, Tim’s journey to India led to a spiritual awakening that completely transformed his approach to wealth management. Now known as “Jai” (meaning “victory” in Hindu), he blends psychology, spirituality, and financial planning to help families create legacies that truly fulfill. This isn’t your typical financial advice episode. Prepare for a deep dive into human archetypes, family genograms, money scripts, and the ancient wisdom that can heal our broken relationship with wealth. From meditation techniques to generational patterns, Jai reveals how to build inner securities equal to your outer securities. Who is Tim? After losing his daughter in 2005, Tim’s journey to India led to a spiritual awakening that completely transformed his approach to wealth management. Now known as “Jai” (meaning “victory” in Hindu), he blends psychology, spirituality, and financial planning to help families create legacies that truly fulfill. Key Takeaways The Psychology of Money Redefining Wealth Know Thyself Framework Conscious Parenting & Money Spiritual Integration The Team Approach Practical Tools Generational Wisdom Connect with Madhavi Facebook : https://www.facebook.com/thinkoutsidethestock LinkedIn : https://www.linkedin.com/in/madhavinadejain/ Youtube : https://www.youtube.com/@thinkoutsidethestock Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

June 5, 20251 hr 5 min

EP 43: Why No One Talks About Land Flipping – And How Jack Bosch Turned It Into a Forever Cash Model!

In this episode of Think Outside the Stocks, Madhavi Jain had a candid conversation withJack Bosch a real estate expert who transformed his humble beginnings as a German immigrant with two suitcases and an almost empty bank account into a multi-million-dollar land flipping empire. Jack, a #1 bestselling author and financial expert, shares how he flipped over 5,000 properties and built the revolutionary “Forever Cash” model, empowering over 1,000 individuals to achieve millionaire status through his educational programs. Jack opens up about his journey from struggling to get started to mastering strategies like seller financing, double closings, and leveraging technology to automate his business. He explains how he turned raw, overlooked land into a consistent wealth-building machine without the hassle of renovations or tenant management. “It’s about seeing opportunity where others see nothing,” Jack says, inviting you to rethink traditional real estate investing. Key topics include: • How flipping raw land can lead to explosive profits • Insider secrets to seller financing and double closing techniques • The creation of the “Forever Cash” model for perpetual wealth • Lessons learned from early mistakes and overcoming investment challenges • The impact of automation and modern tech on scaling a real estate business Whether you’re just starting out or looking to break free from conventional investing, this episode is packed with actionable insights and inspiring stories that challenge the status quo. Plus, enjoy a rapid-fire round where Jack reveals his favorite books, personal insights, and more. Subscribe now to Think Outside the Stocks for expert perspectives that help you think—and invest—differently! Links for Viewers to Connect Jack Bosch: Website: www.landprofitgenerator.com LinkedIn: https://www.linkedin.com/in/jack-bosch-a923b59/ Podcast: https://podcasts.apple.com/us/podcast/the-jack-bosch-show/id980606803 Publication: https://www.amazon.com/Forever-Cash-Earn-Spend-Charge-Everlasting/dp/1614487820 Links for Viewers to Connect Madhavi Jain: Website: https://thinkoutsidethestocks.com/ LinkedIn: https://www.linkedin.com/in/madhavinadejain/ Instagram: https://www.instagram.com/thinkoutsidethestocks/ Youtube: https://www.youtube.com/@thinkoutsidethestock Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

February 12, 202547 min

EP42: 33 Passive Deals and Counting: Lessons from Jeremy Dyer

In this episode of Think Outside the Stocks , Madhavi Jain engages in a compelling conversation with Jeremy Dyer , founder of Starting Point Capital and a distinguished real estate investor, to unveil the top strategies for success in multifamily investing. Jeremy's impressive portfolio includes over 5,000 multifamily units and active participation in 33 passive real estate deals , amounting to more than $750 million in assets under management. His journey from a corporate sales career to a leading figure in real estate syndications offers invaluable lessons for investors at all levels. Key Takeaways from the Episode: Evaluating Investment Opportunities The Significance of Team Dynamics Understanding Financial Metrics Diversification Strategies Adapting to Market Changes Throughout the discussion, Jeremy underscores the importance of trust, transparency, and building strong relationships within the real estate ecosystem. His practical insights can guide both new and experienced investors toward achieving long-term success. Whether you're embarking on your investment journey or looking to refine your existing strategies, this episode provides actionable insights to help you make informed decisions and achieve your financial goals. 👉 Subscribe to Think Outside the Stocks today to access more expert advice and strategies for building wealth through real estate investing! Link for Viewers: Think Outside the Stocks - https://thinkoutsidethestocks.com/ Jeremy's Website- https://www.startingpointcapital.com/ Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.

December 3, 20241 hr 0 min

EP 41: Investing in Syndications? Top Red Flags in Underwriting with Jason Williams

In this episode of Think Outside the Stocks , Madhavi Jain explores multifamily investing with Jason L. Williams, a seasoned expert with over 20 years in real estate. From his chemical engineering background to mastering underwriting, Jason shares key lessons from navigating market shifts and building successful investments. Jason offers insights into protecting capital, understanding deal financials, and spotting red flags in pitch decks. He emphasizes the critical role of team selection, noting that a skilled operator is often the difference between success and failure. "It’s not just about the property," Jason says. "It’s about the team behind it." Key topics include: Why underwriting is essential for passive investors. Common mistakes when evaluating deals. Assessing risk and the value of stress testing. Interest rates, market cycles, and their impact on multifamily investments. Practical strategies for navigating underwriting challenges. Whether you're new or experienced in multifamily investing, this episode offers actionable advice to help you make smarter decisions and avoid pitfalls. Plus, enjoy a rapid-fire round where Jason reveals his favorite books, travel spots, and personal insights. Subscribe now to Think Outside the Stocks for more expert perspectives on real estate investing! Link for Viewers: Think Outside the Stocks - https://thinkoutsidethestocks.com/ Think Outside The Stocks brings you industry experts and guests to share their knowledge and expertise. To invest with them directly, please do your own thorough partner and investment due diligence. To participate in the thoroughly vetted investments and strategic partners alongside us as our passive partners, join our Investor Inner Circle for FREE Access FREE investor education, and join our community in the members-only area. To start your journey, download Active Cashflow with Passive Real Estate Investments . Read the full description at https://thinkoutsidethestocks.com/podcast CONNECT WITH MADHAVI JAIN: LinkedIn , FB or IG Disclaimer: This podcast is for education and information purposes only, not an investment opportunity or financial advice. Please do your own due diligence and consult your tax, legal or financial advisor, etc., to invest.