In this episode, Dave interviews Spencer Hilligoss, co-founder of Madison Investing, who shares his honest journey from a demanding 13-year tech career in Silicon Valley to building a thriving real estate investing business with his wife.

Spencer talks about navigating the reality behind the romanticized vision of real estate investing, overcoming the unexpected challenges of scaling Madison Investing, and the unique advantages (and trials) of running a family business. Hear his candid take on leveraging prior experience from fintech and tech startups, how he creates real, lasting relationships with every investor, and why prioritizing sustainable growth over venture capital-fueled hypergrowth was the right move.

This episode covers actionable entrepreneurship insights—like developing powerful frameworks for decision-making, consistently managing risk in investments, setting habits that actually drive growth, and how staying physically and mentally healthy is vital for any founder. Spencer’s reflections on redefining success, building wealth to serve your life, and the honest ups and downs of the entrepreneurial journey will resonate deeply with anyone building a business.

Don’t miss these lessons in real estate investing, personal productivity, relationship-building, and sustainable entrepreneurship!

Connect with Spencer: https://www.linkedin.com/in/shilligoss/

Learn more about Leverage Assistants: https://www.leverageassistants.com/?via=dave

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