Alternative Investor Mastermind

Jack Krupey

Most accredited real estate investors have the majority of their wealth in the stock market. Investors are at mercy of the volatility and the unexpected roller coaster of ups and downs. They are unaware of the potential returns and benefits of alternative assets such as private real estate. However, growth can only come if you are open to change and new ideas. Who would have thought that you could earn even higher returns by getting into less-explored aspects of alternative investments? Welcome to Alternative Investor Mastermind, a show that covers unique investment opportunities and the lifestyle they can create. Join informative discussions that highlight passive real estate strategies most financial advisors ignore. Unshackle yourself from the bounds of traditional mainstream investments. Now is the time to open doors to brand new opportunities and create Wealth Without Wall Street. These alternatives have been used by many generations to get richer. They have historically outperformed the 8%-10% returns of what people generally get in the stock market. Yet, these kinds of investments are usually out of the spotlight. Since they are often considered "country club deals", you may not know them. Thanks to the internet age and updated SEC regulations around raising capital, these deals are now available to the public. Learn all about how they can make ordinary investors like you become ultra-wealthy and ultra-connected. If you're an accredited investor interested in maximizing your investing strategy, this podcast is here to help you out. Every episode opens your eyes to information and opportunities you may have ignored. Gather actionable tips about getting into syndication, particularly on doing due diligence. Delve into the world of passive investing by going beyond the typical fix and flip deals and into refreshing strategies. Try out multifamily, self-storage spaces, mobile homes, Bitcoin mining, ATM funds, and beyond. Hosting the podcast is Jack Krupey, an experienced real estate executive for more than 20 years. He is the Founder/CEO of JKAM Investments, a company providing access to private advisory services for real estate and alternative investments. Jack focuses on investment and management of different asset classes. Previously a real estate broker, wholesaler, landlord, and Wall Street employee, he transitioned to offering passive investing opportunities to accredited investors.  Throughout his career, Jack expanded his connections. Today, his vast network is composed of long-term relationships with skilled real estate developers, sponsors, and syndicators. Some appear on this podcast to share the valuable lessons from their own investments. Bringing your real estate game to the next level calls for courage to try new things. As an accredited investor, the opportunities around you are limitless. All you have to do is know what to look out for and where. Understanding the full extent of alternatives gives you a head start over other investors stuck with traditional, highly-competitive assets. Once you jump into these not-so-well-known (yet extremely rewarding) deals, do not hesitate to give your all! Join Jack in the exciting episodes of Alternative Investor Mastermind. Listen to the podcast at https://alternativeinvestormastermind.com.

  1. Mastering the Odds: Probability Hacking, AI, and Building a Future-Proof Life

    11/27/2025

    Mastering the Odds: Probability Hacking, AI, and Building a Future-Proof Life

    What if your success isn’t about luck — but math? In this episode, Jack sits down with Kyle Austin Young, author of Success Is a Numbers Game, to break down how probability, intentional planning, and strategic pessimism can radically transform your business, career, and investments. Kyle shares how two back-to-back layoffs pushed him into fractional consulting, how he built a framework to “de-risk” any goal, and why thinking negative may be the most powerful advantage you have. They also dive deep into AI’s impact on jobs, the future of work, real estate investing, social media strategy, and how to tilt the odds in your favor no matter what industry you're in. Whether you're an entrepreneur, investor, or anyone looking to increase your odds of winning, this conversation is packed with practical, actionable insights. CONNECT WITH JACK! LinkedIn: /in/jackkrupey/ Instagram: /jkrupey/ Facebook: /jkrupey/ Podcast: https://www.buzzsprout.com/2139703/share Signup to our newsletter: https://bit.ly/JKAMSub Passive Loss Calculator: https://calc.jkaminvestments.com/ 00:00 – Disclaimer & Intro 00:42 – Meet Kyle Austin Young & His New Book 02:05 – Early Career Setbacks: Two Layoffs in 13 Months 04:12 – From W2 to Fractional Consulting 06:18 – Reinventing Success: The Birth of the Success Diagram 10:10 – Probability Hacking Explained 14:30 – Using AI as the Ultimate Pessimist 18:05 – Marathon Example: Why Your Odds Aren’t What You Think 22:40 – Real-World Application: Solving a Nonprofit’s Mystery Decline 26:50 – AI, Small Business, and the Future of Consulting 30:40 – Easy Hacks vs. Predictive Hacks 36:55 – How Kyle Landed a Director Job at Age 21 41:10 – Investing Insights: Rentals, Land, and Leverage 46:15 – Risk Management for Investors 50:22 – Social Media, Sales, and Why LinkedIn Wins 55:08 – Podcasting as the New Trust Builder 57:45 – Will AI Create Mass Unemployment? 1:01:40 – Why Trust Becomes Your Greatest Asset 1:05:30 – Parting Advice: Think Negative to Win More 1:07:10 – Where to Find Kyle & Final Wrap-Up Instagram | Website | Facebook | Watch on YouTube LOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

    34 min
  2. Beyond Wall Street: Real Estate, Oil & Gas, and the Future of AI Investing

    10/20/2025

    Beyond Wall Street: Real Estate, Oil & Gas, and the Future of AI Investing

    In this episode of The Alternative Investor Mastermind, host Jack Krupey sits down with Dave Wolcott, Founder & CEO of Pantheon Investments, to explore what it really takes to build holistic wealth — beyond Wall Street. From oil & gas investing and AI-driven tax strategies to the launch of Pantheon’s Wealth OS platform, Dave reveals how the ultra-wealthy think differently about taxes, diversification, and purpose-driven success. Whether you’re a real estate investor, a business owner, or simply looking to optimize your financial future, this episode will show you how to align your capital, mindset, and lifestyle to create lasting freedom. Timestamps:  00:00 - Intro  02:30 - Dave’s journey from Marine Corps to investor  07:45 - Tax planning vs tax preparation  12:15 - Real estate and oil & gas tax advantages  19:40 - AI tools transforming tax and wealth management  26:00 - The rise of private credit and energy investing  33:10 - The Holistic Wealth Strategy framework  39:30 - Investing in yourself and building true freedom  45:00 - Outro CONNECT WITH JACK!  LinkedIn: /in/jackkrupey/  Instagram: /jkrupey/  Facebook: /jkrupey/  Podcast: https://www.buzzsprout.com/2139703/share Sign up for our newsletter: https://bit.ly/JKAMSub —  🎧 Listen, like, subscribe, and comment!  #AlternativeInvesting #TaxStrategies #AIWealth #OilAndGasInvesting #PassiveIncome #HolisticWealth #RealEstateInvesting #FinancialFreedom #PrivateCredit #PantheonInvestments Instagram | Website | Facebook | Watch on YouTube LOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

    27 min
  3. 💡 Raise Smarter, Invest Sharper: Private Equity Playbook for 2025 with Jack and Zack

    12/11/2024

    💡 Raise Smarter, Invest Sharper: Private Equity Playbook for 2025 with Jack and Zack

    In this episode of Alternative Investor Mastermind, Jack Krupey and Zack Giarrizzo tackle the most pressing topics for investors, sponsors, and fund managers.  From navigating the challenges of raising capital to understanding the private equity landscape, this episode is packed with actionable insights. Hear the behind-the-scenes story of the Nashville deal, explore the impact of rising interest rates, and discover how investor profiles shape funding strategies. We also cover the emerging "Build-to-Rent" opportunity and the vital role of team dynamics in deal success. Stay ahead of the curve with key financial metrics and the latest underwriting trends. This is your essential guide to the current and future outlook of alternative investments. Navigating the challenges of raising capital - 1:06 Understanding the private equity landscape - 3:36 Success stories: the nashville deal - 6:18 Importance of investor profiles - 9:13 Current market trends and underwriting - 11:50 Key financial metrics today - 14:40 Effects Interest rates in investments - 17:14 Opportunities in build to rent - 20:19 Role of team dynamics in deal success - 22:57 Essential info for sponsors - 25:58 Future outlook - 28:48 🎧 Tune in for expert perspectives and stay ahead of the curve in real estate and alternative investments. CONNECT WITH JACK! LinkedIn:  /in/jackkrupey/ Instagram:   /jkrupey/ Facebook: /jkrupey/ Podcast: https://www.buzzsprout.com/2139703/share Signup to our newsletter: https://bit.ly/JKAMSub Don't forget to like, subscribe, and hit the notification bell to stay updated on future episodes! Instagram | Website | Facebook | Watch on YouTube LOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

    34 min
  4. Weathering the Storm: How Natural Disasters Impact Real Estate Investments

    11/27/2024

    Weathering the Storm: How Natural Disasters Impact Real Estate Investments

    Natural disasters can disrupt real estate markets, damage properties, and cause significant financial setbacks. In this episode of Alternative Investor Mastermind, we explore the critical risks and solutions for real estate investors when disasters strike. Industry experts Jack Krupey and Zack Giarrizzo share their insights on the most vulnerable real estate asset classes during natural disasters, real-life examples of disaster-affected properties, and how to choose the right insurance policies to protect your investments. They also discuss key strategies to minimize financial losses and build disaster-resilient portfolios. Whether you're investing in multifamily properties, industrial real estate, or mobile homes, understanding how to prepare for and recover from natural disasters is essential. CONNECT WITH JACK! LinkedIn:  /in/jackkrupey/ Instagram:   /jkrupey/ Facebook: /jkrupey/ Podcast: https://www.buzzsprout.com/2139703/share Signup to our newsletter: https://bit.ly/JKAMSub 📌 Don't forget to like, comment, and subscribe for more expert insights into alternative real estate investments! #RealEstateInvesting #InsuranceForInvestors #DisasterPreparedness #RealEstateRiskManagement #PassiveIncomeStrategies #AlternativeInvesting #RealEstateInsurance #InvestingTips #RealEstateFinance #WealthBuilding Instagram | Website | Facebook | Watch on YouTube LOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

    17 min
5
out of 5
8 Ratings

About

Most accredited real estate investors have the majority of their wealth in the stock market. Investors are at mercy of the volatility and the unexpected roller coaster of ups and downs. They are unaware of the potential returns and benefits of alternative assets such as private real estate. However, growth can only come if you are open to change and new ideas. Who would have thought that you could earn even higher returns by getting into less-explored aspects of alternative investments? Welcome to Alternative Investor Mastermind, a show that covers unique investment opportunities and the lifestyle they can create. Join informative discussions that highlight passive real estate strategies most financial advisors ignore. Unshackle yourself from the bounds of traditional mainstream investments. Now is the time to open doors to brand new opportunities and create Wealth Without Wall Street. These alternatives have been used by many generations to get richer. They have historically outperformed the 8%-10% returns of what people generally get in the stock market. Yet, these kinds of investments are usually out of the spotlight. Since they are often considered "country club deals", you may not know them. Thanks to the internet age and updated SEC regulations around raising capital, these deals are now available to the public. Learn all about how they can make ordinary investors like you become ultra-wealthy and ultra-connected. If you're an accredited investor interested in maximizing your investing strategy, this podcast is here to help you out. Every episode opens your eyes to information and opportunities you may have ignored. Gather actionable tips about getting into syndication, particularly on doing due diligence. Delve into the world of passive investing by going beyond the typical fix and flip deals and into refreshing strategies. Try out multifamily, self-storage spaces, mobile homes, Bitcoin mining, ATM funds, and beyond. Hosting the podcast is Jack Krupey, an experienced real estate executive for more than 20 years. He is the Founder/CEO of JKAM Investments, a company providing access to private advisory services for real estate and alternative investments. Jack focuses on investment and management of different asset classes. Previously a real estate broker, wholesaler, landlord, and Wall Street employee, he transitioned to offering passive investing opportunities to accredited investors.  Throughout his career, Jack expanded his connections. Today, his vast network is composed of long-term relationships with skilled real estate developers, sponsors, and syndicators. Some appear on this podcast to share the valuable lessons from their own investments. Bringing your real estate game to the next level calls for courage to try new things. As an accredited investor, the opportunities around you are limitless. All you have to do is know what to look out for and where. Understanding the full extent of alternatives gives you a head start over other investors stuck with traditional, highly-competitive assets. Once you jump into these not-so-well-known (yet extremely rewarding) deals, do not hesitate to give your all! Join Jack in the exciting episodes of Alternative Investor Mastermind. Listen to the podcast at https://alternativeinvestormastermind.com.