Alternative Investor Mastermind

Hosted by Jack Krupey

Entrepreneurship EducationInterviews guests

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Episodes

108

Latest episode

Mar 2026

Language

EN-US

About the show

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 .

Listen to episodes

60 recent

March 14, 2026Episode 10730 min

Why 18 Million Rentals Are Struggling (And How Seller Financing Could Replace Them)

Real estate markets are changing fast, and investors who adapt will find the biggest opportunities.In this episode of Alternative Investor Mastermind, Jack Krupi sits down with legendary note investor Eddie Speed, who has been buying and selling mortgage notes since 1980. Together they break down the massive shifts happening in housing today and why seller financing and note investing may be the next major wave in real estate.Eddie explains why millions of landlords are struggling with cash flow, how converting rental properties into seller-financed deals can dramatically improve returns, and why the coming wave of non-performing loans could reshape the investment landscape. They also discuss how technology, blockchain, and AI are transforming the mortgage industry and what that means for investors.Inside the episode:• Why 18 million rental homes may not be cash-flowing anymore • How seller financing can increase returns from ~4% to double-digit yields • The hidden 800,000+ delinquent mortgages not yet in foreclosure • Why note investing historically explodes during market disruptions • How AI is already underwriting mortgage deals and changing the industry • The potential future of blockchain-based mortgage notesIf you're a real estate investor, landlord, note buyer, or passive investor, this conversation reveals where the next opportunities may emerge in today’s evolving market.Listen now to learn how experienced investors are positioning themselves for the next cycle.Instagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

November 27, 2025Episode 10633 min

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/shareSignup to our newsletter: https://bit.ly/JKAMSubPassive Loss Calculator: https://calc.jkaminvestments.com/00:00 – Disclaimer & Intro00:42 – Meet Kyle Austin Young & His New Book02:05 – Early Career Setbacks: Two Layoffs in 13 Months04:12 – From W2 to Fractional Consulting06:18 – Reinventing Success: The Birth of the Success Diagram10:10 – Probability Hacking Explained14:30 – Using AI as the Ultimate Pessimist18:05 – Marathon Example: Why Your Odds Aren’t What You Think22:40 – Real-World Application: Solving a Nonprofit’s Mystery Decline26:50 – AI, Small Business, and the Future of Consulting30:40 – Easy Hacks vs. Predictive Hacks36:55 – How Kyle Landed a Director Job at Age 2141:10 – Investing Insights: Rentals, Land, and Leverage46:15 – Risk Management for Investors50:22 – Social Media, Sales, and Why LinkedIn Wins55:08 – Podcasting as the New Trust Builder57:45 – Will AI Create Mass Unemployment?1:01:40 – Why Trust Becomes Your Greatest Asset1:05:30 – Parting Advice: Think Negative to Win More1:07:10 – Where to Find Kyle & Final Wrap-UpInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

October 20, 2025Episode 10527 min

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 - OutroCONNECT WITH JACK! LinkedIn: /in/jackkrupey/ Instagram: /jkrupey/ Facebook: /jkrupey/ Podcast: https://www.buzzsprout.com/2139703/shareSign up for our newsletter: https://bit.ly/JKAMSub— 🎧 Listen, like, subscribe, and comment! #AlternativeInvesting #TaxStrategies #AIWealth #OilAndGasInvesting #PassiveIncome #HolisticWealth #RealEstateInvesting #FinancialFreedom #PrivateCredit #PantheonInvestmentsInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

August 15, 20254 min

JKAM 2025 Update: New Offerings + Passive Loss Tax Calculator Explained

In this JKAM Investments update, Jack Krupey shares what’s ahead for 2025 — including exciting new investment offerings and our Passive Loss Tax Calculator, designed to help investors maximize their tax efficiency and keep more of what they earn.Whether you’re a seasoned real estate investor or just starting your passive income journey, this update gives you insight into:✅ Upcoming opportunities with JKAM✅ How the Passive Loss Tax Calculator works✅ Why now is the time to position yourself for tax savings💼 Learn more about JKAM Investments: www.jkaminvestments.com📊 Try our Passive Loss Tax Calculator: calc.jkaminvestments.com#JKAMInvestments #PassiveIncome #TaxStrategy #RealEstateInvesting #JackKrupeyInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

December 11, 2024Episode 10433 min

💡 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 - 1:06Understanding the private equity landscape - 3:36Success stories: the nashville deal - 6:18Importance of investor profiles - 9:13Current market trends and underwriting - 11:50Key financial metrics today - 14:40Effects Interest rates in investments - 17:14Opportunities in build to rent - 20:19Role of team dynamics in deal success - 22:57Essential info for sponsors - 25:58Future 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/shareSignup to our newsletter: https://bit.ly/JKAMSubDon't forget to like, subscribe, and hit the notification bell to stay updated on future episodes!Instagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

December 4, 2024Episode 10336 min

Tariffs, Tech, and Tomorrow: Jack & Zack’s Bold Predictions for 2025

In this episode of Alternative Investor Mastermind, Jack Krupey and Zack Giarrizzo dive into the biggest trends shaping 2025. From the potential impact of Bitcoin on global markets to how AI is revolutionizing real estate, we break down the critical shifts every investor should know.We also explore how tariffs could reshape construction costs and housing affordability, plus actionable insights for navigating these challenges. Whether you're a seasoned investor or just starting, this episode is packed with must-know insights for the year ahead.🎧 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/shareSignup to our newsletter: https://bit.ly/JKAMSubDon't forget to like, subscribe, and hit the notification bell to stay updated on future episodes!#RealEstateInvesting #BitcoinTrends #AIinRealEstate #TariffsImpact #AlternativeInvestments #2025Outlook #RealEstateMarket #HousingAffordability #ConstructionTrends #PodcastInsightsInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

November 27, 2024Episode 10216 min

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/shareSignup 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 #WealthBuildingInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

November 20, 2024Episode 10127 min

The Investor’s Marketing Blueprint: Navigating the 4 Challenges Part 2 with Jack Krupey and Scott Corbett

Welcome to Alternative Investor Mastermind!In this episode, hosts Jack Krupey and Scott Corbett explore “Cultural Insights and Humor in Business” while unpacking key lessons from the evolving world of real estate and alternative investments. They share their journey, including:- The Evolution of a Marketing Agency- Collaborative Frameworks for Success- The Power of Mastermind Groups- Networking and Community Building- Reflections on COVID and Its Impact- Our Favorite TV ShowsWith a perfect mix of humor, actionable insights, and relatable stories, Jack and Scott offer a unique perspective on navigating business challenges and finding success through collaboration and creativity.Tune in for an engaging conversation that blends business strategy, culture, and personal growth!CONNECT WITH JACK!LinkedIn: /in/jackkrupey/Instagram: /jkrupey/Facebook: /jkrupey/Podcast: https://www.buzzsprout.com/2139703/shareSignup to our newsletter: https://bit.ly/JKAMSubDon’t forget to like, subscribe, and hit the notification bell to stay updated on future episodes!Instagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

November 13, 2024Episode 10024 min

The Investor’s Marketing Blueprint: Navigating the 4 Challenges Part 1 with Jack Krupey and Scott Corbett

Welcome to Alternative Investor Mastermind! In this episode, hosts Jack Krupey and Scott Corbett dive deep into The Investor’s Marketing Blueprint: Navigating the 4 Challenges. Real estate investors and professionals often face unique marketing hurdles when it comes to alternative investments. Jack and Scott share proven strategies to overcome these obstacles and boost your marketing efforts. Whether you’re scaling your portfolio or just starting out, this episode is packed with actionable insights for investors looking to succeed.CONNECT WITH JACK!LinkedIn: /in/jackkrupey/Instagram: /jkrupey/Facebook: /jkrupey/Podcast: https://www.buzzsprout.com/2139703/shareSignup to our newsletter: https://bit.ly/JKAMSubDon't forget to like, subscribe, and hit the notification bell to stay updated on future episodes!#AlternativeInvesting #RealEstateMarketing #InvestmentMarketing #MarketingForInvestors #PropertyInvesting #RealEstateInvesting #RealEstateTips #MarketingChallenges #InvestmentStrategies #RealEstateProfessionalsInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!

November 6, 2024Episode 9937 min

Real Estate and Politics: Breaking Down Government Regulations that can Affect Your Investments with Jack Krupey and Zack Giarrizzo

In this episode of Alternative Investor Mastermind, Jack Krupey and Zack Giarrizzo dive deep into the critical role government regulations play in shaping the real estate market. From zoning laws and rent controls to tax incentives and new policies emerging from the recent US elections, we explore how these regulations affect investors, developers, and homeowners alike. With the midterms and key elections now behind us, we also analyze the potential impact of the new political landscape on the real estate sector.Join us for expert insights on navigating a rapidly evolving market, how to adapt to shifting policy, and what to expect in the months ahead.Key Topics Discussed:The impact of government regulations on real estate investmentChanges in zoning, property taxes, and rent control lawsWhat the recent US elections mean for the real estate marketStrategies for investors in a politically-charged environmentTune in for valuable tips and actionable strategies to stay ahead of the curve in the real estate market.CONNECT WITH JACK!LinkedIn: /in/jackkrupey/Instagram: /jkrupey/Facebook: /jkrupey/Podcast: https://www.buzzsprout.com/2139703/shareSignup to our newsletter: https://bit.ly/JKAMSubDon't forget to like, subscribe, and hit the notification bell to stay updated on future episodes!#RealEstateRegulations #GovernmentImpactOnRealEstate #USRealEstate2024 #ElectionImpactOnRealEstate #AlternativeInvestorMastermind #RealEstateInvesting #PropertyMarket2024 #ZoningLaws #RealEstateTax #RentControl #RealEstateTrends #ElectionAftermath #PoliticalImpactRealEstate #RealEstateTips #InvestInRealEstateInstagram | Website | Facebook | Watch on YouTubeLOVE THE SHOW? Please subscribe, rate, review, and share! Thank you!