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What if the greatest investment you could make isn't in real estate, stocks, or even private credit—but in yourself? Dave Wolcott, former Marine officer turned alternative investment expert, shares how studying millionaires and billionaires led him to discover a holistic approach to wealth that goes far beyond your bank account. In this episode, Dave breaks down private credit (the hard money lending of the business world), explains why he focuses on just three asset classes, and reveals how investors are achieving 20%+ returns by cutting out the middlemen.

[00:00 - 05:30] From Marines to Triplets: The Wake-Up Call

• Served as an officer in the Marine Corps, traveled the world including Israel
• Had triplets in 2000, quadrupling his family size overnight with an 18-month-old at home

[05:31 - 09:25] The Six Forms of Capital: Beyond Financial Wealth

• The greatest investment is in yourself—not just the next deal
• Defines holistic wealth across six dimensions: financial, intellectual, spiritual, human, emotional, and social capital
  
  
  

[09:26 - 15:05] Private Credit Explained: The Business World's Hard Money Lending

• Banks are tightening regulations, creating gaps in funding for growing small businesses
• Private credit fills the need for fast capital—think roofing companies with 3 years of backlogged work after hurricanes

[15:06 - 20:05] How to Access Institutional-Quality Returns

• Pooling investor capital through a fund model to bring $10M+ to sponsors
• Gets the same terms as major institutions by working directly with sponsors (no middlemen)

[20:06 - 25:10] The Three-Asset Strategy: Real Estate, Energy, and Private Credit

• Ultra-wealthy get really good at 1-3 asset classes for best due diligence and deal flow

[25:11 - 31:00] Time Is the Real Asset

• Questions the accumulation theory: why defer taxes in a 401(k) when taxes will likely increase?

[31:01 - 33:05] Final Four & How to Connect

Connect with Dave:

Website: https://holisticwealthstrategy.com (free book download)

Podcast: Wealth Strategy Secrets of the Ultra Wealthy

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What if the key to successful multifamily investing isn't just about the numbers—but about the people living in your properties? Joe Rinderknecht, the cowboy-hat-wearing founder of Cowboy Capital, shares his unconventional path from shoveling manure on a Utah ranch to operating over 1,000 multifamily units.

[01:40 - 06:15] From Ranch to Real Estate: Building on Grit

• Grew up ranching and breaking horses in northern Utah—learned that your word is your bond
• Father left the ranch for construction and cabinet making, taught Joe everything from concrete to framing

[06:40 - 10:10] Trial by Fire: The 80-Unit Section 42 Property

• Asked for a property management job with zero experience—got thrown into an 80-unit low-income housing property
• Property had no manager for two weeks, with sky-high delinquency, vacancy, crime, drugs, and cockroaches

[10:11 - 15:20] The Path to Becoming a Sponsor

• Never planned to stay in property management long-term—goal was always to learn and move on
• Admits being "unemployable" with a resume showing 6-8 month stints at various companies

[16:35 - 23:35] Impact Investing: Making Every Dollar Matter

• Lost his brother (age 20) and grandmother in a 2013 car accident—nearly died himself
• Provides four types of support: capital, food, construction/home modifications, and mindset coaching

[23:36 - 26:40] Why Treating Tenants Well Is Good Business

• Questions how slumlords succeed when they don't care about people's lives
• When tenants feel like a unit is their home, turnover drops, repairs decrease, delinquency falls

[26:41 - 32:00] Rapid Growth and What's Next

• Bought 4 deals (419 units) since September 2024, currently under contract on 117 more units
• Believes there's a great buying opportunity in the next 10-24 months

[26:45 - 32:55] Final Four & How to Connect

Connect with Joe:

Website: https://cowboycapital.us
Email: Joe@CowboyCapital.us
LinkedIn: Joe Rinderknecht
Instagram: @joe_rinder

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Sometimes the best business decision is knowing when to let go. Amy Calandrino, founder of a commercial real estate brokerage, shares her journey from hammering in her own signs during the 2010 recession to building a team of nearly 10 advisors—and why she ultimately chose to close her firm to join Cushman & Wakefield. In this episode, Amy reveals the hidden costs of entrepreneurship, the importance of aligning your work with your values, and how she's redirecting her energy toward meaningful impact through her family foundation's financial literacy programs.

[01:05 - 04:10] From Vermont to Orlando: Building a Career on Grit

• Started working full-time at age 13 and put herself through college debt-free
• Worked alongside her husband in a law office where she learned about commercial real estate

[04:25 - 07:20] The Hidden Costs of Running a Brokerage

• Founded her brokerage in 2010 during the economic downturn with a shoestring budget
• Grew from solo founder to nearly 10 advisors by 2022

[07:21 - 11:45] Making the Leap: Consulting the Best in the Business

• Sought advice from industry leaders Sarah Malcolm, Allison Weiss, and Beth Azor
• Realized she could still be an entrepreneur without owning a brokerage

[11:46 - 19:30] The Three-Month Transition and Its Unexpected Lessons

• Spent 90 days transitioning clients and wrapping up her brokerage
• Experienced grief despite making the right decision

[19:31 - 27:15] Redirecting Energy: The Aspiring Entrepreneur Program

• Founded a family foundation with her husband to give back to the community
• Created an entrepreneurship program for elementary school students

[27:20 - 31:50] Final Four & How to Connect

Connect with Amy:

LinkedIn: https://www.linkedin.com/in/amycalandrino/

Email: Amy.Calandrino@cushwake.com

Book: "From Perfect to Real" (available on Amazon)

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WHERE CAN I LEARN MORE?

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"Success to me is serving my clients in the best way possible and knowing each and every day that I've put forth the most amount of effort that I can. I never want to p

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