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/
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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

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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

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—
🎧 Listen, like, subscribe, and comment!
#AlternativeInvesting #TaxStrategies #AIWealth #OilAndGasInvesting #PassiveIncome #HolisticWealth #RealEstateInvesting #FinancialFreedom #PrivateCredit #PantheonInvestments

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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 #JackKrupey

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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!

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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/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!

#RealEstateInvesting #BitcoinTrends #AIinRealEstate #TariffsImpact #AlternativeInvestments #2025Outlook #RealEstateMarket #HousingAffordability #ConstructionTrends #PodcastInsights

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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

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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 Shows

With 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/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!

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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/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!

#AlternativeInvesting #RealEstateMarketing #InvestmentMarketing #MarketingForInvestors #PropertyInvesting #RealEstateInvesting #RealEstateTips #MarketingChallenges #InvestmentStrategies #RealEstateProfessionals

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