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Welcome to Target Market Insights. A podcast to help real estate investors navigate neighborhoods through the lens of local experts. In each episode, we speak to local specialists to learn about their market, useful tips, and the latest trends and developments. This show is designed to help you with the insights you need to win your target market.

Jun 30, 2020

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