• John Casmon

How to Evaluate Multifamily Sponsors with Spencer Hilligoss, Episode 204



Spencer Hilligoss worked a full-time job in technology so he opted to invest passively in real estate. Starting with a duplex in the Bay Area, then turnkey rentals in the Midwest, before focusing on passive apartment syndications. Spencer managed to work his full-time job and invest passively until he was earning enough from his passive investments to become a full-time real estate investor. Spencer and his wife Jennifer are partners in over 5,000 units, valued at over $600 million. Now, he has launched Madison Investing to help others invest in multifamily.



Key Takeaways:

  • Exposed to real estate at a young age as his parents were in real estate. Worked open houses as a kid, made him run to the technology field

  • Quit his technology leadership career right before Covid19 hit and is a passive and active full-time real estate investor

  • Worked at LendingTree and learned how much investors make on deals piqued his interest in REI

  • How he found his first rental property in 2016 and pulled a ‘newbie” move that didn’t give him the cashflow he wanted

  • The importance of underwriting skills

You can build the perfect plan, but success comes down to the operator
  • Understanding the 3 pillar framework of analyzing a market: Team, market, and deal

  • Why deal analysis should include more analysis about the “who” in the deal

  • Why Spencer invests in multifamily properties vs. turnkey properties

  • The best question to ask a sponsor operator to gain valuable insight into their work ethic and business values

  • Evaluating risk factors in a deal

  • Spencer answers today’s biggest question: Why should I invest in real estate during COVID19?

  • The challenges of investing and running 5000+ units


Bullseye Tips


Apparent Failure:

The way we conduct ourselves in business when times are bad is when your true qualities shine through.


Digital/Mobile Resource:

Syndicated Deal Analyzer


Most Recommended Book:

Rich Dad, Poor Dad by Robert Kiyosaki


Daily Habit:

Calendar blocking


Wish I Knew When I Was Starting Out:

Understanding goal setting on cash flow


Current Curiosity:

Education within the real estate sphere


Best Place to Grab a Bite in Alameda, CA:

The Tavern


Contact Spencer:

Madison Investing

LinkedIn