The Truth About Cash Flow, Tax Strategies, and Risk in Alternative Investments

Today's episode features a dynamic conversation with Spencer Hilligoss, Founder of Madison Investing, and your host, Dave Wolcott—serial entrepreneur and author of the bestselling book "The Holistic Wealth Strategy." Spencer brings a wealth of experience as both a technologist and seasoned real estate investor, having gone full cycle on over 20 private real estate deals across asset classes like multifamily, self-storage, and medical office. Together, Spencer and Dave help investors cut through the market noise and navigate the complexities of alternative investments.

In this educational and insightful discussion, Spencer and Dave candidly share their personal investing journeys and the key lessons they've learned from recent shifts in the real estate landscape—especially in the wake of rapidly rising interest rates and tightening commercial debt markets. They emphasize that building true wealth requires strategic planning, rigorous due diligence, and thoughtful risk management, especially when promises of cash flow and "preferred returns" might not be as certain as they seem.

Listeners will gain practical advice on how to evaluate deals, spot pitfalls, and leverage the collective wisdom of investment communities. Spencer also shares how to align investment choices with your unique "Investor DNA" and long-term vision, rather than chasing shiny objects or relying on projections alone.

In this episode, we discuss:

1. The truth behind cash flow projections and preferred returns

2. How depreciation and tax strategies impact real estate investments

3. The risks and nuances of preferred equity and rescue funds

4. Practical portfolio construction and recession-proofing your wealth strategy

Learn more: https://pantheoninvest.com/episode195

Get Dave's Free Book: https://holisticwealthstrategy.com/

Connect with Spencer:

• Business website: www.madisoninvesting.com
• Personal bio website: www.spencerhilligoss.com
• LinkedIn profile: www.linkedin.com/in/shilligoss/
• Twitter: x.com/SpenceHilligoss