Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

306: How To Invest Privately and Grow Strategically with Spencer Hilligoss

In this episode, Spencer Hilligross explores the journey into passive investing and why accredited individuals can begin confidently as limited partners. He highlights how curiosity and selective learning are far more important than consuming endless books or podcasts, empowering investors to avoid burnout while still gaining the knowledge they need.

Spencer also shares valuable lessons from vetting sponsors and investing across different market conditions. His experiences—from home-run full-cycle deals to uncomfortable challenges—reveal the reality that no framework is perfect, but consistent due diligence helps investors navigate uncertainty with greater clarity.The conversation takes a deeper turn as Spencer reflects on his Silicon Valley career and the myth of the life-changing startup exit. After multiple attempts without the expected payoff, he recognized the need for a more systematic approach to wealth building. His story underscores why relying solely on a W-2 income is far less viable today, and why intentional investing is essential for long-term financial freedom.

In this episode, you will hear:

Why passive investing is a strong entry point for accredited individuals
How curiosity fuels smarter investing decisions
Why vetting sponsors requires both structure and real-world experience
What full-cycle wins and losses teach investors over time
Why Silicon Valley’s “lottery mentality” rarely pays off
How to build a more systematic path toward financial freedom
In this episode, you will hear:

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